HCID 18434148, compound → HCID 18434219, compound

HRID 2306469Notes

Reaction equation

HRID 2306469 reaction equation
[CH:1]([Mg]Cl)=[CH2:2].C[Si](C)(C)[O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]([C:16]2[CH:21]=[CH:20][C:19]([Br:22])=[CH:18][CH:17]=2)=[O:15])=[CH:10][CH:9]=1>C1COCC1.C1(C)C=CC=CC=1>[Br:22][C:19]1[CH:20]=[CH:21][C:16]([C:14]([C:11]2[CH:12]=[CH:13][C:8]([OH:7])=[CH:9][CH:10]=2)([OH:15])[CH:1]=[CH2:2])=[CH:17][CH:18]=1

Participants

5

Reactant 2

HCID 18434148HCID 18434148, compoundHCID 178461836HCID 178461836, compound

Product 1

HCID 18434219HCID 18434219, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Eb) 30.2 ml of 15% vinylmagnesium chloride solution in THF are added dropwise at 0° C. to a solution of 5.58 g of 4-trimethylsilyloxyphenyl-(4-bromo-phenyl)-methanone in 80 ml of toluene. The mixture is stirred at 0° C. for 2 h., then at room temperature for 2 h., subsequently hydrolyzed with 40 ml of ammonium chloride solution and extracted with methylene chloride. The extracts are dried, evaporated and purified over silica gel with toluene-acetone as the eluent. There are obtained 2.8 g of (RS)-4-[1-(4-bromo-phenyl)-1-hydroxy-allyl]-phenol, MS: m/e 304 (M+H+, 1Br).

Workup

  1. waitat room temperature for 2 h.
  2. extractionsubsequently hydrolyzed with 40 ml of ammonium chloride solution and extracted with methylene chloride
  3. customThe extracts are dried
  4. customevaporated
  5. custompurified over silica gel with toluene-acetone as the eluent

Sources & evidence

ORD record
ord-ab74117569fc467aa4350388018d916b
Source dataset
uspto-grants-2002_08
Patent number
US06441177B1

Reaction notes

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