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

HRID 1381252Notes

Reaction equation

HRID 1381252 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-11oxodibenz[b,e]oxepin-2-acetate in 150 ml. of dry ether is added dropwise to 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-2e2ef5679b644b4db3379dceba949b9d
Source dataset
uspto-grants-1986_04
Patent number
US04585788

Reaction notes

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