Sodium borohydride → 1-(2-Chloronaphthalen-1-yl)ethanol

HRID 912028Notes

Reaction equation

HRID 912028 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]=1[C:12](=[O:14])[CH3:13].[BH4-].[Na+]>CCO>[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]=1[CH:12]([OH:14])[CH3:13]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 674028271-(2-Chloro-1-naphthalenyl)ethanone

Product 1

HCID 2307821-(2-Chloronaphthalen-1-yl)ethanol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To an EtOH (70 ml) solution of 1-(2-Chloronaphthalen-1-yl)-ethanone (3.98 mmol; prepared according to J. Org. Chem. 1946, 11, 163-169) was added sodium borohydride (232 mg, 6.09 mmol). The mixture was stirred at rt under an atmosphere of nitrogen for one hour. After that time, the mixture was quenched with saturated NH4Cl followed by water, extracted with EtOAc (3×50 ml). The extracts were washed with water (50 ml), brine (50 ml), and dried over MgSO4. After concentration in vacuo, a beige oil was obtained. It was purified by chromatography on silica gel (25 g) eluting with an EtOAc/hexane gradient to give the title compound as a colorless oil. 1H NMR (400 MHz, CDCl3): δ=1.44 (d, J=6.4 Hz, 3H), 2.33 (d, J=3.6 Hz, 1H), 5.97-6.06 (m, 1H), 7.39 (d, J=8.8 Hz, 1H), 7.45-7.58 (m, 2H), 7.67 (d, J=8.8 Hz, 1H), 7.81 (dd, J=1.6, 8.0 Hz, 1H), 8.75 (d, J=8.0 Hz, 1H). MS (ES+): 189.19/191.20 [MH+−H2O]. HPLC: tR=3.38 min (polar—5 min, ZQ3).

Workup

  1. customAfter that time, the mixture was quenched with saturated NH4Cl
  2. extractionextracted with EtOAc (3×50 ml)
  3. washThe extracts were washed with water (50 ml), brine (50 ml)
  4. dry with materialdried over MgSO4
  5. concentrationAfter concentration in vacuo
  6. customa beige oil was obtained
  7. customIt was purified by chromatography on silica gel (25 g)
  8. washeluting with an EtOAc/hexane gradient

Sources & evidence

ORD record
ord-7927cdb8baa2479abe6d6b234548a440
Source dataset
uspto-grants-2011_09
Patent number
US08022206B2

Reaction notes

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