(R)-2-Oxo-2-phenylethyl-3-decanoyloxytetradecanoate → (R)-3-decanoyloxytetradecanoic acid

HRID 1022293Notes

Reaction equation

HRID 1022293 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

HCID 86648296(R)-2-Oxo-2-phenylethyl-3-decanoyloxytetradecanoate

Product 1

HCID 10810916(R)-3-decanoyloxytetradecanoic acidYield 89%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

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).

Workup

  1. temperaturethe mixture heated
  2. temperatureto reflux for 4 h
  3. customThe acetic acid was removed under vacuum
  4. customthe residue azeotroped with toluene to dryness
  5. customThe residue was purified by chromatography on silica gel (120 g RediSep column
  6. washeluting with a gradient of 0% through 60% ethyl acetate/hexanes over 50 min

Sources & evidence

ORD record
ord-646cd34867ff460d91b5f0bab9358ff3
Source dataset
uspto-grants-2014_05
Patent number
US08722064B2

Reaction notes

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