Sodium borohydride → HCID 9907292, compound

HRID 1647499Notes

Reaction equation

HRID 1647499 reaction equation
[C:1]([C:5]1[CH:6]=[CH:7][C:8]2[O:12][C:11]([C:13](=[O:26])[CH2:14][O:15][C:16]3[CH:21]=[CH:20][C:19]([C:22]([O:24][CH3:25])=[O:23])=[CH:18][CH:17]=3)=[CH:10][C:9]=2[CH:27]=1)([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+]>CO>[C:1]([C:5]1[CH:6]=[CH:7][C:8]2[O:12][C:11]([CH:13]([OH:26])[CH2:14][O:15][C:16]3[CH:21]=[CH:20][C:19]([C:22]([O:24][CH3:25])=[O:23])=[CH:18][CH:17]=3)=[CH:10][C:9]=2[CH:27]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 4311764Sodium borohydride2×HCID 15337968HCID 15337968, compound

Product 1

HCID 9907292HCID 9907292, compoundYield 96.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-tert-Butyl-2-(4-methoxycarbonylphenoxyacetyl)benzofuran (124 g) was suspended in 980 ml of methanol and, with cooling with ice and stirring, 30 g of sodium borohydride was added thereto little by little. After stirring for 2 hours, 8.8 g of sodium borohydride was added and the mixture was stirred at room temperature for 4 hours. The reaction mixture was poured into 10 liters of ice water (acidified with hydrochloric acid) and the resulting crystals were collected by filtration. The crystals were dissolved in chloroform, the solution was washed with water twice and the chloroform layer was dried over anhydrous magnesium sulfate followed by concentrating in vacuo to give 120.1 g of crystals. M.p. 110°-112° C.

Workup

  1. temperaturewith cooling with ice
  2. stirringAfter stirring for 2 hours
  3. stirringthe mixture was stirred at room temperature for 4 hours
  4. filtrationthe resulting crystals were collected by filtration
  5. dissolutionThe crystals were dissolved in chloroform
  6. washthe solution was washed with water twice
  7. dry with materialthe chloroform layer was dried over anhydrous magnesium sulfate
  8. concentrationby concentrating in vacuo

Sources & evidence

ORD record
ord-e8376dc0fab2483ca868c93120f501ba
Source dataset
uspto-grants-1995_07
Patent number
US05432195

Reaction notes

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