Chloroform → HCID 14626271, compound

HRID 477784Notes

Reaction equation

HRID 477784 reaction equation
[CH3:1][Si:2]([CH3:24])([C:20]([CH3:23])([CH3:22])[CH3:21])[O:3][C:4]1[CH:19]=[CH:18][C:7]2[O:8][CH2:9][C:10]3[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=3[C:12](=[O:13])[C:6]=2[CH:5]=1.[BH4-].[Na+].C(Cl)(Cl)Cl>CO>[CH3:1][Si:2]([CH3:24])([C:20]([CH3:22])([CH3:21])[CH3:23])[O:3][C:4]1[CH:19]=[CH:18][C:7]2[O:8][CH2:9][C:10]3[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=3[CH:12]([OH:13])[C:6]=2[CH:5]=1

Participants

5

Reactant 3

HCID 6212ChloroformHCID 4311764Sodium borohydrideHCID 14626270HCID 14626270, compound

Product 1

HCID 14626271HCID 14626271, compoundYield 81.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 5 g of 2-(dimethyl-t-butylsilyloxy)-6,11-dihydrodibenz[b,e]oxepin-11-one in 50 ml of methanol is cooled to 0° C. After adding 2 g of sodium borohydride and the mixture is stirred for 1 hour, 300 ml of chloroform is added and the mixture is washed with water and a saturated saline solution, followed by drying over magnesium sulfate. The solvent is distilled off under reduced pressure and the residue is subjected to silica-gel chromatography and eluted with toluene to give 4.1 g of 2-(dimethyl-t-butylsilyloxy)-6,11-dihydrodibenz[b,e]oxepin-11-ol (oil). Mass spectrum m/z: 342(M+).

Workup

  1. washthe mixture is washed with water
  2. dry with materialby drying over magnesium sulfate
  3. distillationThe solvent is distilled off under reduced pressure
  4. washeluted with toluene

Sources & evidence

ORD record
ord-ae58c03dffaa4905a520cdd956e91efc
Source dataset
uspto-grants-1989_12
Patent number
US04889858

Reaction notes

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