Sodium borohydride → 2,3,4,5-Tetrahydro-alpha-methyl-1-benzoxepine-7-methanol

HRID 37413Notes

Reaction equation

HRID 37413 reaction equation
[CH3:1][C:2]([C:4]1[CH:5]=[CH:6][C:7]2[O:13][CH2:12][CH2:11][CH2:10][CH2:9][C:8]=2[CH:14]=1)=[O:3].[BH4-].[Na+]>CO>[CH3:1][CH:2]([C:4]1[CH:5]=[CH:6][C:7]2[O:13][CH2:12][CH2:11][CH2:10][CH2:9][C:8]=2[CH:14]=1)[OH:3]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 133015981-(2,3,4,5-Tetrahydrobenzo[b]oxepin-7-yl)ethanone

Product 1

HCID 199353892,3,4,5-Tetrahydro-alpha-methyl-1-benzoxepine-7-methanolYield 81.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

6.90 g of 2,3,4,5-tetrahydro-1-benzoxepin-7-yl methyl ketone in 60 ml of methanol were treated portionwise with 2.33 g of sodium borohydride (NaBH4) at 0° C. while stirring. After a half hour the reaction mixture was poured on to ice, extracted with ether. The extract was washed with water, dried and evaporated. Chromatography on silica gel (petroleum ether/ethyl acetate 8:2) yielded 5.71 g of 2,3,4,5-tetrahydro-α-methyl-1-benzoxepine-7-methanol as a colorless oil.

Workup

  1. additionAfter a half hour the reaction mixture was poured on to ice
  2. extractionextracted with ether
  3. washThe extract was washed with water
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-2ba826bb731a48e8b1feb8bae02a01c2
Source dataset
uspto-grants-1995_05
Patent number
US05420273

Reaction notes

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