Methanol → HCID 4003528, compound

HRID 477781Notes

Reaction equation

HRID 477781 reaction equation
[CH3:1][O:2][C:3]1[CH:18]=[CH:17][C:6]2[O:7][CH2:8][C:9]3[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=3[C:11](=[O:12])[C:5]=2[CH:4]=1.CO.[BH4-].[Na+]>C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[CH:18]=[CH:17][C:6]2[O:7][CH2:8][C:9]3[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=3[CH:11]([OH:12])[C:5]=2[CH:4]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 677942HCID 677942, compoundHCID 4311764Sodium borohydride

Product 1

HCID 4003528HCID 4003528, compoundYield 89.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 10 g of 2-methoxy-6,11-dihydrodibenz[b,e]oxepin-11-one [Monatsh. Chem., 93, 889 (1962)]in 100 ml of methanol is cooled to 0° C. Thereto 3 g of sodium borohydride is added and the mixture is stirred for 1 hour. After completion of the reaction, chloroform is added and the mixture is washed with a saturated saline solution. After drying over magnesium sulfate and the solvent is distilled off under reduced pressure, the residue is subjected to a silica-gel chromatography and eluted with toluene to give 9 g of the objective compound as an oily product. Mass spectrum m/z: 242(M+).

Workup

  1. additionis added
  2. washthe mixture is washed with a saturated saline solution
  3. dry with materialAfter drying over magnesium sulfate
  4. distillationthe solvent is distilled off under reduced pressure
  5. washeluted with toluene

Sources & evidence

ORD record
ord-7716bc1cf967494480fc969eb71d9234
Source dataset
uspto-grants-1989_12
Patent number
US04889858

Reaction notes

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