Isoxepac → 2-(6,11-Dihydrodibenz[b,e]oxepin-2-yl)ethanol

HRID 1417095Notes

Reaction equation

HRID 1417095 reaction equation
O=[C:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH2:6][O:5][C:4]2[CH:13]=[CH:14][C:15]([CH2:17][C:18](O)=[O:19])=[CH:16][C:3]1=2.B.O1CCCC1>O1CCCC1>[CH:16]1[C:3]2[CH2:2][C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=3[CH2:6][O:5][C:4]=2[CH:13]=[CH:14][C:15]=1[CH2:17][CH2:18][OH:19]

Participants

4

Reactant 2

HCID 41448IsoxepacHCID 2723981Borane;tetrahydrofuran

Product 1

HCID 107287482-(6,11-Dihydrodibenz[b,e]oxepin-2-yl)ethanolYield 15.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 6,11-dihydro-11-oxodibenz[b,e]oxepin-2-acetic acid (100 g) in 450 ml dry tetrahydrofuran (THF) at -5° C. was treated with a 1M solution of borane-THF complex (373 ml in THF) under a nitrogen blanket. After stirring at ambient temperature for 72 hours, the reaction was quenched with methanol then diluted with water. Evaporation of the organic phase left an oily biphase which was basified with saturated sodium bicarbonate and extracted into dichloromethane. The organic phase was dried and evaporated to an oil which was purified by flash chromatography to give 14 g of 2-(6,11-dihydrodibenz[b,e]oxepin-2-yl)ethanol as an oil.

Workup

  1. customthe reaction was quenched with methanol
  2. additionthen diluted with water
  3. customEvaporation of the organic phase
  4. waitleft an oily biphase which
  5. extractionextracted into dichloromethane
  6. customThe organic phase was dried
  7. customevaporated to an oil which
  8. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-da485effc2a34210b4fc7bae25980eff
Source dataset
uspto-grants-1999_06
Patent number
US05917057

Reaction notes

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