Oxalyl chloride → HCID 53822961, compound

HRID 1870583Notes

Reaction equation

HRID 1870583 reaction equation
C([Si]([O:8][C:9](=O)[CH:10]=[CH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[O:18][Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20])(C)C)(C)(C)C.C(Cl)(=O)C([Cl:30])=O>CN(C=O)C.C(Cl)Cl>[C:22]([Si:19]([CH3:21])([CH3:20])[O:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[CH:11]=[CH:10][C:9]([Cl:30])=[O:8])([CH3:25])([CH3:24])[CH3:23]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 53990259HCID 53990259, compound

Product 1

HCID 53822961HCID 53822961, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a 0° C. cold solution of 6.3 g of 3-[2-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-acrylic acid tert-butyl-dimethyl-silyl ester and 8 drops of DMF in 15 ml of CH2Cl2 was added dropwise 2.0 ml of oxalyl chloride. After complete addition the reaction mixture was allowed to warm to room temperature and stirring was continued for 60 h. The reaction mixture was filtered, evaporated to dryness and taken up in MTBE. The solution was cooled in the refrigerator overnight, filtered and evaporated to yield 4.4 g of 3-[2-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-acryloyl chloride.

Workup

  1. additionAfter complete addition the reaction mixture
  2. filtrationThe reaction mixture was filtered
  3. customevaporated to dryness
  4. temperatureThe solution was cooled in the refrigerator overnight
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-daebd2009bed4fbc8175afccacd39185
Source dataset
uspto-grants-2000_08
Patent number
US06096918

Reaction notes

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