Ethyl Acetate → Ethyl 4-(m-methoxyphenyl)-3-phenyl-3-hydroxybutyrate

HRID 2307901Notes

Reaction equation

HRID 2307901 reaction equation
C[Si](C)(C)N[Si](C)(C)C.[Li].[C:11]([O:14][CH2:15][CH3:16])(=[O:13])[CH3:12].[C:17]1([C:23]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([O:32][CH3:33])[CH:27]=2)=[O:24])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C1COCC1>[CH3:33][O:32][C:28]1[CH:27]=[C:26]([CH2:25][C:23]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)([OH:24])[CH2:12][C:11]([O:14][CH2:15][CH3:16])=[O:13])[CH:31]=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 27596142-(3-Methoxyphenyl)-1-phenylethan-1-oneHCID 57426343Lithium bis(trimethylsilyl)amide

Product 1

HCID 22602685Ethyl 4-(m-methoxyphenyl)-3-phenyl-3-hydroxybutyrateYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

Lithium hexamethyldisilazane (88.5 mL, 88.5 mmol) was added to THF (150 mL) at −78° C. After 15 minutes, ethyl acetate (7.79 g, 88.5 mmol) was added over 10 minutes and stirred at −78° C. for 30 minutes. The m-methoxybenzyl phenyl ketone in (10.0 g, 44.25 mmol) THF (100 mL) was added over 15 minutes and kept at that temperature for 3 hours. The reaction mixture was quenched at that temperature with saturated ammonium chloride (15 mL). The reaction mixture was diluted with ether (200 mL) and the organic layer was washed with brine, (100 mL), dried and concentrated to afford the desired product (12 g, 86% yield). NMR was consistent with the desired structure.

Workup

  1. waitkept at that temperature for 3 hours
  2. customThe reaction mixture was quenched at that temperature with saturated ammonium chloride (15 mL)
  3. additionThe reaction mixture was diluted with ether (200 mL)
  4. washthe organic layer was washed with brine, (100 mL)
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-741a0c3575fa4f5482cefdb9d0c1fdf9
Source dataset
uspto-grants-2004_12
Patent number
US06833366B1

Reaction notes

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