Water → 3-(3,4-Dichlorophenyl)-3-butenol t-butyldimethylsilyl ether

HRID 1275155Notes

Reaction equation

HRID 1275155 reaction equation
[CH3:1]C(C)([O-])C.[K+].[Si:7]([O:14][CH2:15][CH2:16][C:17]([C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([Cl:26])[CH:20]=1)=O)([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8].O>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1C=CC=CC=1>[Si:7]([O:14][CH2:15][CH2:16][C:17]([C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([Cl:26])[CH:20]=1)=[CH2:1])([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8]

Participants

6

Reactant 3

HCID 962WaterHCID 11198381HCID 11198381, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 108712633-(3,4-Dichlorophenyl)-3-butenol t-butyldimethylsilyl etherYield 59.1%

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 241BenzeneSolvent2×

Procedure

215 g (0.60 mole) of methyltriphenylphosphonium bromide and 54 g (0.48 mole) of potassium t-butoxide were added to 2 liters of dried benzene, and the mixture was stirred for 9 hours at room temperature. At the end of this time, 40 g (0.12 mole) of 3-(3,4-dichlorophenyl)-3-oxo-1-propanol t-butyldimethylsilyl ether [prepared as described in step (b) above] were dissolved in 800 ml of benzene and the resulting solution was slowly added dropwise to the mixture over a period of 2.5 hours. 1 liter of water was then added to the reaction mixture, and the mixture was stirred for 30 minutes, whilst ice-cooling. The organic layer was separated, and then washed with water and with a saturated aqueous solution of sodium chloride, after which it was dried over anhydrous sodium sulfate. The solvent was removed by distillation under reduced pressure, and the resulting residue was purified by silica gel column chromatography, using hexane as the eluent, to give 23.5 g of the title compound. The physicochemical properties of this product were the same as those of the product produced as described in Example 1(b).

Workup

  1. additionthe resulting solution was slowly added dropwise to the mixture over a period of 2.5 hours
  2. stirringthe mixture was stirred for 30 minutes, whilst ice-
  3. temperaturecooling
  4. customThe organic layer was separated
  5. washwashed with water and with a saturated aqueous solution of sodium chloride
  6. dry with materialafter which it was dried over anhydrous sodium sulfate
  7. customThe solvent was removed by distillation under reduced pressure
  8. customthe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-6ecae7d55928494a8a39e1be12647765
Source dataset
uspto-grants-2000_12
Patent number
US06159967

Reaction notes

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