Benzyl Alcohol → HCID 86709898, compound

HRID 341330Notes

Reaction equation

HRID 341330 reaction equation
[CH3:1][Si:2]([CH3:9])([CH3:8])[CH:3]=[CH:4][C:5]([OH:7])=[O:6].[CH2:10](O)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C1(N=C=NC2CCCCC2)CCCCC1.Cl>ClCCl.CN(C)C1C=CN=CC=1>[CH3:1][Si:2]([CH3:9])([CH3:8])[CH:3]=[CH:4][C:5]([O:7][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:6]

Participants

7

Reactant 4

HCID 244Benzyl AlcoholHCID 313Hydrochloric AcidHCID 10868DicyclohexylcarbodiimideHCID 541719853-(Trimethylsilyl)prop-2-enoic acid

Product 1

HCID 86709898HCID 86709898, compoundYield 94.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 3-trimethylsilylacrylic acid (510 mg, 3.54 mmol) [J. Org. Chem., 56, pp. 4766-4772, 1991] in dichloromethane (8 ml) was added successively with benzyl alcohol (0.59 ml, 5.71 mmol), dicyclohexylcarbodiimide (DCC, 914 mg, 4.44 mmol) and 4-dimethylaminopyridine (4-DMAP, 43 mg, 0.352 mmol) under ice cooling, the mixture was stirred for 5 minutes, and then stirring was further continued at room temperature for 16 hours. The reaction mixture was cooled on ice, and then added with aqueous hydrochloric acid (1 N, 5 ml), the mixture was filtered under reduced pressure, and the resulting urea was washed with ethyl acetate. After the layers were separated, the organic layer was washed with saturated aqueous sodium hydrogencarbonate and water, and dried over anhydrous sodium sulfate, and the solvent was evaporated. The residue was purified by silica gel chromatography [hexane/ethyl acetate (24:1)] to obtain benzyl 3-trimethylsilylacrylate (782 mg, 94%) mentioned in the title as colorless oil.

Workup

  1. stirringstirring
  2. waitwas further continued at room temperature for 16 hours
  3. temperatureThe reaction mixture was cooled on ice
  4. filtrationthe mixture was filtered under reduced pressure
  5. washthe resulting urea was washed with ethyl acetate
  6. customAfter the layers were separated
  7. washthe organic layer was washed with saturated aqueous sodium hydrogencarbonate and water
  8. dry with materialdried over anhydrous sodium sulfate
  9. customthe solvent was evaporated
  10. customThe residue was purified by silica gel chromatography [hexane/ethyl acetate (24:1)]

Sources & evidence

ORD record
ord-3c590d4653d641acb6b2065f40f398fb
Source dataset
uspto-grants-2014_11
Patent number
US08895769B2

Reaction notes

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