Hexamethyldisilazane → HCID 18434188, compound

HRID 2306468Notes

Reaction equation

HRID 2306468 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([Br:16])=[CH:12][CH:11]=2)=[O:9])=[CH:4][CH:3]=1.[CH3:17][Si](C)(C)N[Si](C)(C)C>>[Br:16][C:13]1[CH:14]=[CH:15][C:10]([C:8]([C:5]2[CH:6]=[CH:7][C:2]([OH:1])=[CH:3][CH:4]=2)([OH:9])[CH3:17])=[CH:11][CH:12]=1

Participants

3

Reactant 2

HCID 13838HexamethyldisilazaneHCID 4570728(4-Bromophenyl)(4-hydroxyphenyl)methanone

Product 1

HCID 18434188HCID 18434188, compound

Procedure

Ea) A mixture of 2.77 g of 4-hydroxyphenyl-(4-bromo-phenyl)-methanone and 50 ml of hexamethyldisilazane is heated under reflux for 4 h., then concentrated and dried. The resulting 4-trimethylsilyloxyphenyl-(4-bromo-phenyl)-methanone is dissolved in 60 ml of toluene and treated at room temperature under argon with 11 ml of methylmagnesium chloride solution (22% in THF). The mixture is boiled under reflux. After cooling the mixture is treated with saturated aqueous ammonium chloride solution and extracted with ethyl acetate. The organic phases are washed with saturated sodium chloride solution and dried. After evaporation of the ethyl acetate extracts there are obtained 3.36 g of (RS)-4-[1-(4-bromo-phenyl)-1-hydroxy-ethyl]-phenol, MS: m/e 293 (M+H+, 1Br).

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 4 h.
  3. concentrationconcentrated
  4. customdried
  5. dissolutionThe resulting 4-trimethylsilyloxyphenyl-(4-bromo-phenyl)-methanone is dissolved in 60 ml of toluene
  6. additiontreated at room temperature under argon with 11 ml of methylmagnesium chloride solution (22% in THF)
  7. temperatureunder reflux
  8. temperatureAfter cooling the mixture
  9. additionis treated with saturated aqueous ammonium chloride solution
  10. extractionextracted with ethyl acetate
  11. washThe organic phases are washed with saturated sodium chloride solution
  12. customdried
  13. customAfter evaporation of the ethyl acetate

Sources & evidence

ORD record
ord-c4beaad091a6486a9c6d430043912195
Source dataset
uspto-grants-2002_08
Patent number
US06441177B1

Reaction notes

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