Sodium borohydride → HCID 12330038, compound

HRID 1195029Notes

Reaction equation

HRID 1195029 reaction equation
[BH4-].[Na+].[O:3]=[C:4]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[CH2:8][O:7][C:6]2[CH:15]=[CH:16][C:17]([CH2:19][C:20]([O:22][CH3:23])=[O:21])=[CH:18][C:5]1=2>CO>[OH:3][CH:4]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[CH2:8][O:7][C:6]2[CH:15]=[CH:16][C:17]([CH2:19][C:20]([O:22][CH3:23])=[O:21])=[CH:18][C:5]1=2

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 10333952Methyl (11-oxo-6,11-dihydrodibenzo[b,e]oxepin-2-yl)acetate

Product 1

HCID 12330038HCID 12330038, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1.4 g. of sodium borohydride, 200 ml. of methanol, and 4.0 g. of methyl 6,11-dihydro-11-oxodibenz[b,e]oxepin-2-acetate is stirred at 5°-10° for four hours and then the methanol is removed under high vacuum. Water and tetrahydrofuran are added to the residue, and the solution is adjusted to a pH of 5-6 with the addition of acetic acid and stirred for two hours at room temperature. The mixture is extracted with chloroform, and the chloroform solution is dried over sodium sulfate and concentrated. Trituration of the solid with ether provides methyl 6,11-dihydro-11-hydroxydibenz[b,e]oxepin-2-acetate as colorless crystals, m.p. 85°-87°.

Workup

  1. customthe methanol is removed under high vacuum
  2. additionWater and tetrahydrofuran are added to the residue
  3. additionthe solution is adjusted to a pH of 5-6 with the addition of acetic acid
  4. extractionThe mixture is extracted with chloroform
  5. dry with materialthe chloroform solution is dried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-1280a5f7f35b48b4a309abadb4c6d3f3
Source dataset
uspto-grants-1989_03
Patent number
US04816591

Reaction notes

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