(R)-2-Oxo-2-phenylethyl-3-decanoyloxytetradecanoate → (R)-3-decanoyloxytetradecanoic acid
Reaction equation
O=[C:2]([C@@:6](CCC1C=CC=CC=1)([O:18][C:19](=[O:29])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[C:3]([O-:5])=[O:4]>C(O)(=O)C.[Zn]>[C:19]([O:18][C@H:6]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH2:2][C:3]([OH:5])=[O:4])(=[O:29])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
Ester 39 (10.15 g, 20.77 mmol) was dissolved in acetic acid (100 mL). Zinc (15.5 g, 237 mmol) was added, and the mixture heated to reflux for 4 h. The acetic acid was removed under vacuum and the residue azeotroped with toluene to dryness. The residue was purified by chromatography on silica gel (120 g RediSep column, eluting with a gradient of 0% through 60% ethyl acetate/hexanes over 50 min, 85 mL/min) to give the product 40 (7.2 g, 89%) as a colorless liquid. 1H NMR (300 MHz, CDCl3) δ 5.23-5.19 (m, 1H), 2.62-2.55 (m, 2H), 2.34-2.25 (m, 2H), 1.65-1.58 (m, 2H), 1.28-1.20 (m, 32H), 0.85 (m, 6H).