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

HRID 1944054Notes

Reaction equation

HRID 1944054 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, 2H), 6.99-7.02 (m, 2H), 3.58 (d, J=5.8 Hz, 2H), 1.30 (s, 6H).

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-64c5d28bea4a4a29ab6c77f9d2294516
Source dataset
uspto-grants-2013_03
Patent number
US08394819B2

Reaction notes

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