Borane → Methyl 2-(4-fluorophenethyl)-5-hydroxymethylbenzoate

HRID 2228027Notes

Reaction equation

HRID 2228027 reaction equation
[F:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][CH2:7][C:8]2[CH:16]=[CH:15][C:11]([C:12](O)=[O:13])=[CH:10][C:9]=2[C:17]([O:19][CH3:20])=[O:18])=[CH:4][CH:3]=1.O1CCCC1.B>CO>[F:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][CH2:7][C:8]2[CH:16]=[CH:15][C:11]([CH2:12][OH:13])=[CH:10][C:9]=2[C:17]([O:19][CH3:20])=[O:18])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6331BoraneHCID 8028Tetrahydrofuran2×HCID 184746364-(4-Fluorophenethyl)-3-methoxycarbonylbenzoic acid

Product 1

HCID 18474618Methyl 2-(4-fluorophenethyl)-5-hydroxymethylbenzoateYield 82.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 4-(4-fluorophenethyl)-3-methoxycarbonylbenzoic acid (16.5 g, 54.88 mmol), tetrahydrofuran(500 ml) and borane in tetrahydrofuran (1M, complex, 218 ml, 218 mmol) was stirred under an inert atmosphere at reflux for 6 hours. The reaction was cooled to ambient temperature and methanol (1 L) was added. It was then evaporated to dryness to give a dark oil which was purified by flash chromatography using iso-hexane/ethyl acetate (1:1) as eluant to give as a clear gum methyl 2-(4-fluorophenethyl)-5-hydroxymethylbenzoate (13.10 g).

Workup

  1. temperatureat reflux for 6 hours
  2. customIt was then evaporated to dryness
  3. customto give a dark oil which
  4. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-cd1691f083d24cdd9bc097d63defab19
Source dataset
uspto-grants-2002_07
Patent number
US06414145B1

Reaction notes

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