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

HRID 357259

Reaction equation

HRID 357259 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>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

3

Reactant 1

HCID 41448Isoxepac

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

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 boran-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-177df3b30ccc470ea6504ea2584e3ab5
Source dataset
uspto-grants-1998_11
Patent number
US05840749

Linked notes

Loading…