Sodium borohydride → HCID 69054129, compound

HRID 2102992Notes

Reaction equation

HRID 2102992 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:11](=[C:12]([CH3:15])[C:13]=1[CH3:14])[O:10][CH2:9][C:6]1([CH2:8][CH2:7]1)[C:5]2=[O:16].[BH4-].[Na+]>CO>[CH3:14][C:13]1[C:12]([CH3:15])=[C:11]2[C:4]([CH:5]([OH:16])[C:6]3([CH2:9][O:10]2)[CH2:8][CH2:7]3)=[CH:3][C:2]=1[OH:1]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 69053342HCID 69053342, compound

Product 1

HCID 69054129HCID 69054129, compoundYield 62.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 6-hydroxy-7,8-dimethyl-4H-spiro[chromene-3,1′-cyclopropan]-4-one (150 mg) and sodium borohydride (50 mg) in MeOH (15 mL) was stirred at room temperature for 2 h. After evaporation, the residue was applied to silica gel column eluting with 30-60% EtOAc in hexane to give 7,8-dimethyl-4H -spiro[chromene-3,1′-cyclopropane]-4,6-diol as an off-white solid (95 mg).

Workup

  1. customAfter evaporation
  2. washeluting with 30-60% EtOAc in hexane

Sources & evidence

ORD record
ord-78c26b2d3a1149aa8bd44852302ba1db
Source dataset
uspto-grants-2009_08
Patent number
US07576094B2

Reaction notes

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