Sodium borohydride → 6-Chloro-3,4-dihydro-4-hydroxy-spiro[2H-1-benzopyran-2,1'-cyclobutane]

HRID 1175759Notes

Reaction equation

HRID 1175759 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[CH:5]=[CH:6][C:7]2[O:15][C:11]3([CH2:14][CH2:13][CH2:12]3)[CH2:10][C:9](=[O:16])[C:8]=2[CH:17]=1>CO>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]2[O:15][C:11]3([CH2:12][CH2:13][CH2:14]3)[CH2:10][CH:9]([OH:16])[C:8]=2[CH:17]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 667465206-Chlorospiro[chroman-2,1'-cyclobutan]-4-one

Product 1

HCID 667463666-Chloro-3,4-dihydro-4-hydroxy-spiro[2H-1-benzopyran-2,1'-cyclobutane]

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

Sodium borohydride (40 mmol) was added to a solution of 6-Chloro-3,4-dihydro-4-oxo-spiro[2H-1-benzopyran-2,1′-cyclobutane] (10 mmol) in methanol (10 ml). at about 0° C. and the reaction mixture was stirred at room temperature for about 2 h and compound was extracted in ethyl acetate. Organic layer was washed with water, brine and separated. It was then dried on anhydrous sodium sulfate and concentrated to afford the desired product as a white solid.

Workup

  1. extractioncompound was extracted in ethyl acetate
  2. washOrganic layer was washed with water, brine
  3. customseparated
  4. dry with materialIt was then dried on anhydrous sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-83e3f64ff7d3473c9a4e37f6fbdd4e0d
Source dataset
uspto-grants-2010_11
Patent number
US07842703B2

Reaction notes

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