Lithium borohydride → 2-(4-Fluorophenyl)-2-methylpropan-1-ol

HRID 570676Notes

Reaction equation

HRID 570676 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:14])([CH3:13])[C:9](OC)=[O:10])=[CH:4][CH:3]=1.[Li+].[BH4-]>C1COCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([CH3:14])([CH3:13])[CH2:9][OH:10])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 66617112Methyl 2-(4-fluorophenyl)-2-methylpropanoate

Product 1

HCID 212628022-(4-Fluorophenyl)-2-methylpropan-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The ester from step 1 was reduced by dissolving in THF (0.15 M) and treating with LiBH4 (5 eq.) and stirring for 15 hours. The reaction mixture was quenched with water and extracted with DCM, the organic layer dried (Na2SO4) and concentrated to provide oily 2-(4-fluorophenyl)-2-methylpropan-1-ol: 1H NMR (600 MHz, CDCl3) δ 7.31-7.34 (m, 2 H), 6.99-7.02 (m, 2 H), 3.58 (d, J=5.8 Hz, 2 H), 1.30 (s, 6 H).

Workup

  1. customThe reaction mixture was quenched with water
  2. extractionextracted with DCM
  3. dry with materialthe organic layer dried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-ea169fea1a21468e9ed429e6ef6bb77d
Source dataset
uspto-grants-2015_05
Patent number
US09023864B2

Reaction notes

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