Methyl 4-benzoylbutyrate → 1-Phenylpentane-1,5-diol

HRID 550338Notes

Reaction equation

HRID 550338 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[O:7]=[C:8]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:9][CH2:10][CH2:11][C:12](OC)=[O:13]>O1CCCC1>[C:16]1([CH:8]([OH:7])[CH2:9][CH2:10][CH2:11][CH2:12][OH:13])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 137042Methyl 4-benzoylbutyrateHCID 21226445Aluminium lithium hydride

Product 1

HCID 2638501-Phenylpentane-1,5-diol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A 2.0 M tetrahydrofuran solution of lithium aluminum hydride (2.80 mL, 5.60 mmol) was added to a tetrahydrofuran solution (10 mL) of methyl 5-oxo-5-phenylpentanoate (500 mg, 2.78 mmol) at 0° C. The reaction mixture was stirred for one hour and quenched with the sequential addition of water (0.2 mL), 10% sodium hydroxide solution (0.2 mL), and water (0.6 mL). It was concentrated in vacuo to give the title compound as a colorless oil. 1H NMR (500 MHz, CDCl3) δ 1.32-1.42 (m, 1H), 1.46-1.55 (m, 1H), 1.56-1.64 (m, 2H), 1.70-1.78 (m, 1H), 1.78-1.88 (m, 1H), 3.63 (t, J=6.6 Hz, 2H), 4.68 (dd, J=5.7, 7.8 Hz, 1H), 7.25-7.30 (m, 1H), 7.32-7.35 (m, 4H).

Workup

  1. customquenched with the sequential addition of water (0.2 mL), 10% sodium hydroxide solution (0.2 mL), and water (0.6 mL)
  2. concentrationIt was concentrated in vacuo

Sources & evidence

ORD record
ord-ea0e54a1e67343ccbe3eb3eedef79c41
Source dataset
uspto-grants-2011_05
Patent number
US07947664B2

Reaction notes

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