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Leading Question

An excellent place to start, methinks.

Mechanism

Show me the molecules!

Experimental

How we know, what we know. You can see it, you're already here!

NMR Data

Does this rag smell like CDCl3 to you?

References

Good old fashioned proof.

Biographies

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New Disaster

I wonder how long Ruchika can hold the entire world.

 

The monoacid 67 (5.65 g, 25.2 mmol) was dissolved in 70 mL of i-PrOH. After it was dissolved completely, DMAP (.19g, .16 mmol) and DMT-MM (9.07g, 32.76 mmol) was added to the solution. It was then stirred for 3 hours at 50 degress Celcius, and allowed to dry until fully concentrated. The remaining product was dissolved in ethyl acetate, then washed with two units of 125mL of HCl.

The organic layers were dried with Na2SO4 and evaporated to give the diester product. This was a yellow oil (7.9g) which was dissolved in THF/H2O (1:1 300mL), LiOH (0.79g, 34.4mmol) was added and the solution was stirred at room temperature. TLC was used in this step to determine progress. Two hours later, more LiOH(.1g) was added to the mixture. This completely consumed the starting material, and then the reaction was quenched with two units of 200mL of HCl. The mixture was extracted with EtOAc (2x 250mL) and dried over MgSO4. EtOAc was removed by reducing the pressure and the remaining oil was the product.

It was dissolved in THF (100mL) and benzylamine (3.33g, 32.12mmol) was added. After stirring for five minutes, DMT-MM (8.89g, 32.12mmol) was added. This resulted in a white suspension that was stirred for 3 hours at room temperature until the reaction was completed. This was confirmed by TLC analysis. From this product, the solvent was removed and the remaining residue was dissolved in EtOAc and then washed with two units of HCl (200mL). The organic layer was dried again over MgSO4, this left a solid yellow product.

After purification the remaining product, (+)-78: IR (film) νmax 3297,1706, 1618, 1540, 1382, 1273, 1107, 696 cm-1; 1H NMR (400 MHz, CDCl3) δ 7.98 (bs,1H), 7.33-7.28 (m, 5H), 7.02 (d, J = 5.2 Hz, 1H), 6.86 (d, J = 5.2 Hz, 1H), 5.08 (sep, 1H),4.52 (ABX, J = 14.8 Hz, J = 6 Hz, υAB = 20.4 Hz, 2H ), 1.84 (s, 3H), 1.80 (s, 3H), 1.26,(d, J = 6.4 Hz, 3H), 1.21 (d, J = 6.4 Hz, 3H); 13C NMR (100 MHz, CDCl3) δ 164.8,163.4, 160.7, 150.0, 147.2, 146.1, 138.0, 128.8, 127.9, 127.6, 92.9, 91.7, 69.8, 43.6, 21.8(2 C), 16.2, 15.7 (2 sets of equivalent carbons on benzyl group).

Product