3-(2-Fluorophenyl)propanoic acid → 3-(2-Fluorophenyl)propan-1-ol

HRID 446403Notes

Reaction equation

HRID 446403 reaction equation
CSC.B.[F:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:12][CH2:13][C:14](O)=[O:15]>O1CCCC1>[F:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:12][CH2:13][CH2:14][OH:15]

Participants

4

Reactant 2

HCID 20638663-(2-Fluorophenyl)propanoic acidHCID 12423031(Dimethyl sulfide)trihydroboron

Product 1

HCID 126185173-(2-Fluorophenyl)propan-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Borane dimethyl sulfide complex (2M in THF, 27.6 mL) was added dropwise to a solution of 3-(2-fluorophenyl)propanoic acid (3.09 g) in tetrahydrofuran (25 mL) and the resulting mixture was allowed to warm to RT and stirred overnight. The reaction was cautiously quenched with methanol and when bubbling had ceased, evaporated. The residue was purified by flash silica chromatography eluting with 4:1 to 1:1 isohexane:ethyl acetate gradient to give the subtitled compound as a clear oil. Yield 2.72 g.

Workup

  1. customThe reaction was cautiously quenched with methanol and when
  2. custombubbling
  3. customevaporated
  4. customThe residue was purified by flash silica chromatography
  5. washeluting with 4:1 to 1:1 isohexane

Sources & evidence

ORD record
ord-eb498b45bde648f1aa85017e56cb4eaa
Source dataset
uspto-grants-2013_07
Patent number
US08476265B2

Reaction notes

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