Hydrochloric Acid → 5-Chloro-2,3-dihydro-1H-inden-1-ol

HRID 582925Notes

Reaction equation

HRID 582925 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[CH2:6][CH2:5]2.[OH-].[Na+].[BH4-].[Na+].Cl>O.C1COCC1>[OH:11][CH:7]1[C:8]2[C:4](=[CH:3][C:2]([Cl:1])=[CH:10][CH:9]=2)[CH2:5][CH2:6]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 1425995-Chloro-1-indanoneHCID 4311764Sodium borohydride

Product 1

HCID 225048045-Chloro-2,3-dihydro-1H-inden-1-olYield 83%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
2.5 °C

Procedure

A mixture of 2.5 g of 5-chloroindan-1-one and 30 ml of THF is cooled to 0-5° C., 2.5 ml of concentrated NaOH solution and then, in portions, 0.88 g of sodium borohydride are added and the reaction mixture is stirred overnight at RT. It is poured into 100 ml of water, the mixture is acidified to pH 2 by the addition of concentrated HCl solution, extracted with AcOEt, the organic phase is washed with saturated NaCl solution and dried over Na2SO4 and the solvent is evaporated off under vacuum. The residue is chromatographed on silica using a cyclohexane/AcOEt mixture (80/20; v/v) to give 2.1 g of the expected product.

Workup

  1. extractionextracted with AcOEt
  2. washthe organic phase is washed with saturated NaCl solution
  3. dry with materialdried over Na2SO4
  4. customthe solvent is evaporated off under vacuum
  5. customThe residue is chromatographed on silica using a cyclohexane/AcOEt mixture (80/20; v/v)

Sources & evidence

ORD record
ord-3c979d0db6d44c47a6d47fc5f9d8de67
Source dataset
uspto-grants-1999_07
Patent number
US05925768

Reaction notes

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