Methyl (11-oxo-6,11-dihydrodibenzo[b,e]oxepin-2-yl)acetate → HCID 12330037, compound

HRID 1195040Notes

Reaction equation

HRID 1195040 reaction equation
[O:1]=[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](OC)=[O:19])=[CH:16][C:3]1=2.[H-].[Al+3].[Li+].[H-].[H-].[H-]>CCOCC>[OH:1][CH: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][CH2:18][OH:19])=[CH:16][C:3]1=2

Participants

4

Reactant 2

HCID 10333952Methyl (11-oxo-6,11-dihydrodibenzo[b,e]oxepin-2-yl)acetateHCID 21226445Aluminium lithium hydride

Product 1

HCID 12330037HCID 12330037, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 3.5 g. of methyl 6,11-dihydro-11-oxodibenz[b,e]oxepin-2-acetate in 150 ml. of dry ether is added dropwise to a stirred suspension of 2.5 g. of lithium aluminum hydride in 50 ml. of dry ether. The mixture is refluxed for three hours, cooled to 0° C., and hydrolyzed. The mixture is extracted with ether, dried over sodium sulfate, and evaporated to a crude crystalline product. Recrystallization from acetonitrile provides colorless crystals, m.p. 135°-137° C. of 6,11-dihydro-11-hydroxydibenz[b,e]oxepin-2-ethanol.

Workup

  1. temperatureThe mixture is refluxed for three hours
  2. extractionThe mixture is extracted with ether
  3. dry with materialdried over sodium sulfate
  4. customevaporated to a crude crystalline product
  5. customRecrystallization from acetonitrile

Sources & evidence

ORD record
ord-f7e4752354e54b63bf9ccb2ad294a70f
Source dataset
uspto-grants-1989_03
Patent number
US04816591

Reaction notes

Loading…