Lithium borohydride → [3-(Cyclopropylmethyl)phenyl]methanol

HRID 1510123Notes

Reaction equation

HRID 1510123 reaction equation
[CH:1]1([CH2:4][C:5]2[CH:6]=[C:7]([CH:12]=[CH:13][CH:14]=2)[C:8](OC)=[O:9])[CH2:3][CH2:2]1.[BH4-].[Li+]>C1COCC1>[CH:1]1([CH2:4][C:5]2[CH:6]=[C:7]([CH2:8][OH:9])[CH:12]=[CH:13][CH:14]=2)[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 57336624Methyl 3-(cyclopropylmethyl)benzoate

Product 1

HCID 57336625[3-(Cyclopropylmethyl)phenyl]methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of methyl 3-(cyclopropylmethyl)benzoate (9.06 g, 47.6 mmol) in THF (100 mL) was added lithium borohydride (2.0 M in THF, 71.4 mL, 142.9 mmol). After stirring at 50° C. for 1 h the reaction was cooled, quenched with excess methanol and concentrated under vacuum. Purification by silica gel chromatography (30% EtOAc/hexanes) afforded the desired product.

Workup

  1. temperaturewas cooled
  2. customquenched with excess methanol
  3. concentrationconcentrated under vacuum
  4. customPurification by silica gel chromatography (30% EtOAc/hexanes)

Sources & evidence

ORD record
ord-6094dd8edd2144a7a9b63d0ea5eb6e88
Source dataset
uspto-grants-2012_07
Patent number
US08211904B2

Reaction notes

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