Dimethyl malonate → dimethyl (S)-alpha-(1,3-diphenyl-2-propen-1-yl)malonate

HRID 658287

Reaction equation

HRID 658287 reaction equation
C(O[CH:5]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH:6]=[CH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)(=O)C.[C:20]([O:27][CH3:28])(=[O:26])[CH2:21][C:22]([O:24][CH3:25])=[O:23].C/C(/O[Si](C)(C)C)=N\[Si](C)(C)C.C([O-])(=O)C.[K+].[Cl-].[NH4+]>ClCCl.C(OCC)C>[C:14]1([C@H:5]([CH:21]([C:20]([O:27][CH3:28])=[O:26])[C:22]([O:24][CH3:25])=[O:23])[CH:6]=[CH:7][C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

8

Reactant 5

HCID 7943Dimethyl malonateHCID 25517Ammonium ChlorideHCID 517044Potassium AcetateHCID 6058773-Acetoxy-1,3-diphenylpropeneHCID 6913588N,O-bis(trimethylsilyl)acetamide

Product 1

HCID 45115416dimethyl (S)-alpha-(1,3-diphenyl-2-propen-1-yl)malonate

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

In 0.5 ml of dichloromethane were suspended 0.9 mg (2.5 μmol) of [PdCl(η3-C3H5)]2 and 1.8 mg (5.5 μmol) of (R,R)-t-Bu-QuinoxP* (1), followed by stirring at room temperature for 10 to 30 minutes. To the resulting solution were added a solution of 126 mg (0.50 mmol) of 1,3-diphenyl-2-propenyl acetate in 1.5 ml of dichloromethane, 171 μl (1.50 mmol) of dimethyl malonate, 367 μl (1.50 mmol) of N,O-bis(trimethylsilyl)acetamide (BSA), and a trace amount of potassium acetate. The reaction system was stirred at room temperature for 1 hour. The reaction mixture was diluted with diethyl ether, and a saturated aqueous solution of ammonium chloride was added to stop the reaction. The resulting mixture was extracted with diethyl ether, and the organic layer was washed with a sodium chloride aqueous solution. The organic layer was dried over anhydrous sodium sulfate. Any volatile matter was evaporated off, and the residue was purified by silica gel column chromatography.

Workup

  1. stirringThe reaction system was stirred at room temperature for 1 hour
  2. customthe reaction
  3. extractionThe resulting mixture was extracted with diethyl ether
  4. washthe organic layer was washed with a sodium chloride aqueous solution
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. customAny volatile matter was evaporated off
  7. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-0b47e6b8dd0c4e6cba6470c6760811ac
Source dataset
uspto-grants-2011_12
Patent number
US08076480B2

Linked notes

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