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

HRID 471202Notes

Reaction equation

HRID 471202 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

A solution of borane dimethylsulfide 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 quenched with methanol and, when bubbling had ceased, evaporated. Purification was by silica gel chromatography eluting with 4:1 to 1:1 isohexane:ethyl acetate gradient. The fractions containing product were combined and evaporated in vacuo to give the subtitled compound as a clear oil. Yield 2.72 g.

Workup

  1. customThe reaction was quenched with methanol and, when
  2. custombubbling
  3. customevaporated
  4. customPurification
  5. washeluting with 4:1 to 1:1 isohexane
  6. additionThe fractions containing product
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-aafbc7363e97457da9893e425f91645f
Source dataset
uspto-grants-2014_01
Patent number
US08629271B2

Reaction notes

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