Phenacyl bromide → (R)-2-Oxo-2-phenylethyl 3-hydroxytetradecanoate

HRID 1022292Notes

Reaction equation

HRID 1022292 reaction equation
[OH:1][C@H:2]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH2:3][C:4]([OH:6])=[O:5].C(N(CC)CC)C.Br[CH2:26][C:27]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:28]>C(OCC)(=O)C>[OH:1][C@H:2]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH2:3][C:4]([O:6][CH2:26][C:27](=[O:28])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:5]

Participants

5

Reactant 3

HCID 6259Phenacyl bromideHCID 8471TriethylamineHCID 5288266(R)-3-hydroxytetradecanoic acid

Product 1

HCID 10690046(R)-2-Oxo-2-phenylethyl 3-hydroxytetradecanoateYield 72%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (R)-3-hydroxytetradecanoic acid (36, see preparation below) (9.55 g, 39.1 mmol) and triethylamine (5.90 g, 58.6 mmol) in ethyl acetate (500 mL) was added 2-bromoacetophenone (7.90 g, 39.1 mmol) at room temperature. The mixture was stirred at room temperature for 14 h. The precipitate was removed by filtration, and the filtrate was concentrated in vacuo. The residue was purified by silica gel chromatography (120 g RediSep column, eluting with a gradient of 0% through 30% ethyl acetate/hexanes over 50 min, 85 mL/min) to give the product 37 (10.2 g, 72% yield) as a white solid.

Workup

  1. customThe precipitate was removed by filtration
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was purified by silica gel chromatography (120 g RediSep column
  4. washeluting with a gradient of 0% through 30% ethyl acetate/hexanes over 50 min

Sources & evidence

ORD record
ord-873ebfc1a0f24da0a4708384b9b8a56c
Source dataset
uspto-grants-2014_05
Patent number
US08722064B2

Reaction notes

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