Ethyl Acetate → HCID 86751395, compound

HRID 1489368Notes

Reaction equation

HRID 1489368 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:3]=1[CH:4]=O.[Si:11]([O:18][CH:19]([CH2:25][C:26](=[O:34])[CH2:27]P(OC)(OC)=O)[CH2:20][C:21]([O:23][CH3:24])=[O:22])([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12].C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>C(O)(C)C>[Si:11]([O:18][CH:19]([CH2:25][C:26](=[O:34])/[CH:27]=[CH:4]/[C:3]1[CH:6]=[CH:7][C:8]([Cl:10])=[CH:9][C:2]=1[Cl:1])[CH2:20][C:21]([O:23][CH3:24])=[O:22])([C:14]([CH3:16])([CH3:15])[CH3:17])([CH3:13])[CH3:12]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 134042,4-DichlorobenzaldehydeHCID 13891275HCID 13891275, compound

Product 1

HCID 86751395HCID 86751395, compoundYield 94.5%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
22 °C

Procedure

In 10 mL of isopropanol (water content: 9,500 ppm) were dissolved 457 mg (2.6 mmol.) of 2,4-dichlorobenzaldehyde and 1.0 g (2.6 mmol.) of methyl 3-[(tert-butyldimethylsilyl)oxy]-6-(dimethoxyphosphinyl)-5-oxohexanoate to give an alcoholic solution. To the alcoholic solution was added 362 mg (2.3 mmol) of potassium carbonate, and the mixture was stirred for 3 hours at room temperature (22° C.). To the resulting reaction mixture was added 40 mL of ethyl acetate, and the mixture was stirred and washed with 20 mL of water. The washing was repeated twice. The organic phase was separated, dried over anhydrous magnesium sulfate, and filtered to give a filtrate. The filtrate was concentrated under reduced pressure, and the residue was subjected to silica gel column chromatography (eluent:hexane/ethyl acetate=95/5, volume ratio) to give 1.06 g (yield: 94%) of methyl (E)-3-[(tert-butyldimethylsilyl)oxy]-7-(2,4-dichlorophenyl)-5-oxo-6-heptenoate.

Workup

  1. customto give an alcoholic solution
  2. customTo the resulting reaction mixture
  3. stirringthe mixture was stirred
  4. washwashed with 20 mL of water
  5. customThe organic phase was separated
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customto give a filtrate
  9. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-7200793a45ff4cfbaaa1bb18036f04d8
Source dataset
uspto-grants-1997_10
Patent number
US05677455

Reaction notes

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