Borane → 3-(4-Fluorophenyl)propan-1-ol

HRID 1592320Notes

Reaction equation

HRID 1592320 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:12])C(O)=O)=[CH:4][CH:3]=1.B.C1C[O:17][CH2:16]C1>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:12][CH2:16][OH:17])=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 6331BoraneHCID 8028Tetrahydrofuran2×HCID 27239152-(4-Fluorophenyl)propionic acid

Product 1

HCID 137472413-(4-Fluorophenyl)propan-1-ol

Procedure

para-Fluorophenylpropionic acid (5.15 g, 31.0 mmol, 1 eq.) was dissolved in THF (150 mL). To this solution a 1.0 M solution of borane in THF was added dropwise (caution—exothermic) at 25° C. under N2. The mixture was refluxed overnight. The reaction was quenched with excess 1N HCl and extracted 3 times with EtOAc. The organic layers were dried (MgSO4), and stripped to yield 5.67 g of a pink oil. Evaporative distillation at 0.05 mmHg and 193-260° C. yielded 2.32 g of product as a clear colorless oil.

Workup

  1. temperatureThe mixture was refluxed overnight
  2. customThe reaction was quenched with excess 1N HCl
  3. extractionextracted 3 times with EtOAc
  4. dry with materialThe organic layers were dried (MgSO4)

Sources & evidence

ORD record
ord-2c262332c60648b8b310bde89c9e9925
Source dataset
uspto-grants-2007_11
Patent number
US07291744B2

Reaction notes

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