Sodium borohydride → HCID 58566761, compound

HRID 1909532Notes

Reaction equation

HRID 1909532 reaction equation
[CH3:1][C:2]1([CH3:19])[CH2:6][C:5]2[CH:7]=[C:8]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:9]=[C:10]([CH:11]=[O:12])[C:4]=2[O:3]1.[BH4-].[Na+]>CO>[CH3:1][C:2]1([CH3:19])[CH2:6][C:5]2[CH:7]=[C:8]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:9]=[C:10]([CH2:11][OH:12])[C:4]=2[O:3]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 58566765HCID 58566765, compound

Product 1

HCID 58566761HCID 58566761, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To an ice cold solution of 2,2-dimethyl-5-phenyl-2,3-dihydrobenzofuran-7-carbaldehyde (545) (1 g, 3.96 mmol) in methanol (20 mL) was added portion wise sodium borohydride (179.9 mg, 4.76 mmol). The resulting mixture was stirred at 0° C. for 3 hours, quenched slowly with water. The product was extracted with dichloromethane. The organic layer was separated, dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (20% EtOAc in hexanes) to provide (2,2-dimethyl-5-phenyl-2,3-dihydrobenzofuran-7-yl)methanol (546).

Workup

  1. customquenched slowly with water
  2. extractionThe product was extracted with dichloromethane
  3. customThe organic layer was separated
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography on silica gel (20% EtOAc in hexanes)

Sources & evidence

ORD record
ord-2ba22649c4b549caac941a285e9a3501
Source dataset
uspto-grants-2013_12
Patent number
US08598374B2

Reaction notes

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