Acetyl chloride → HCID 69143608, compound

HRID 1766862Notes

Reaction equation

HRID 1766862 reaction equation
[OH:1][CH:2]([CH2:9][CH2:10][C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1)=[O:12])[C:3]([O:5][CH2:6][CH:7]=[CH2:8])=[O:4].[C:23](Cl)(=[O:25])[CH3:24].C(=O)([O-])O.[Na+].C(OCC)(=O)C>N1C=CC=CC=1.CCCCCC>[C:23]([O:1][CH:2]([CH2:9][CH2:10][C:11]([O:13][CH2:14][C:15]1[CH:16]=[CH:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=1)=[O:12])[C:3]([O:5][CH2:6][CH:7]=[CH2:8])=[O:4])(=[O:25])[CH3:24]

Participants

7

Reactant 4

HCID 6367Acetyl chlorideHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 69143601HCID 69143601, compound

Product 1

HCID 69143608HCID 69143608, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8058HexaneSolvent

Procedure

Allyl 2-hydroxy-5-[(4-methoxybenzyl)oxy]-5-oxopentanoate (1.26 g, 4.09 mmol) obtained from Example 2-(2) was dissolved in pyridine (15 ml) at 0° C., and acetyl chloride (481.2 mg, 6.13 mmol) was added thereto. The mixture was warmed to room temperature and stirred for 30 minutes, and then, after cooling to 0° C., a saturated aqueous solution of sodium hydrogen carbonate was added thereto followed by extraction of the product with ethyl acetate. The organic layer was washed with a dilute aqueous solution of hydrochloric acid and with a saturated aqueous solution of sodium chloride, and the solvent was distilled off under reduced pressure to give an oily residue. The residue was subjected to chromatography on a silica gel (60 g) column (eluent; ethyl acetate:hexane=1:5) to afford the title compound (1.36 g, 95% yield) as a colorless oil.

Workup

  1. temperatureafter cooling to 0° C.
  2. extractionthereto followed by extraction of the product with ethyl acetate
  3. washThe organic layer was washed with a dilute aqueous solution of hydrochloric acid and with a saturated aqueous solution of sodium chloride
  4. distillationthe solvent was distilled off under reduced pressure
  5. customto give an oily residue

Sources & evidence

ORD record
ord-b761b6ce6f5343df8aa5e4fed06d66f6
Source dataset
uspto-grants-2007_06
Patent number
US07230023B2

Reaction notes

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