Sodium borohydride → HCID 14580514, compound

HRID 2271071Notes

Reaction equation

HRID 2271071 reaction equation
[BH4-].[Na+].[N+:3]([C:6]1[CH:7]=[CH:8][C:9]2[O:15][CH2:14][CH2:13][CH2:12][C:11](=[O:16])[C:10]=2[CH:17]=1)([O-:5])=[O:4]>CO>[N+:3]([C:6]1[CH:7]=[CH:8][C:9]2[O:15][CH2:14][CH2:13][CH2:12][CH:11]([OH:16])[C:10]=2[CH:17]=1)([O-:5])=[O:4]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 145805137-Nitro-3,4-dihydro-1-benzoxepin-5(2H)-one

Product 1

HCID 14580514HCID 14580514, compoundYield 85.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

10.2 g of sodium borohydride were added in portions at 0° C. with vigorous stirring to a suspension of 50 g of 3,4-dihydro-7-nitro-1-benzoxepin-5(2H)-one (J. Chem. Soc., Perkin Trans. 1 (1991), 2763) in 345 ml of methanol. After 30 min, the reaction mixture was added to ice water, the solid was filtered off with suction and 43 g of 7-nitro-2,3,4,5-tetrahydro-1-benzoxepin-5-ol was obtained. This was heated on a water separator for 2 h with 1 g of p-toluenesulfonic acid in 520 ml of toluene. After cooling, the organic phase was washed with sodium bicarbonate solution and sodium chloride solution. After drying over sodium sulfate and concentrating, 38.8 g of 2,3-dihydro-7-nitro-1-benzoxepine were obtained, m.p. 98-100° C.

Workup

  1. filtrationthe solid was filtered off with suction

Sources & evidence

ORD record
ord-b264bd33a93f4cc9acb1e3617f3c9db5
Source dataset
uspto-grants-2001_12
Patent number
US06333349B1

Reaction notes

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