Acetic Anhydride → HCID 53791239, compound

HRID 1741843Notes

Reaction equation

HRID 1741843 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:17]([OH:21])[CH:18]([CH3:20])[CH3:19])[CH:5]=[CH:6][C:7]=1[CH:8]([O:13][CH2:14][O:15][CH3:16])[CH2:9][CH2:10][CH2:11][CH3:12].[C:22](OC(=O)C)(=[O:24])[CH3:23]>>[C:22]([O:21][CH:17]([C:4]1[CH:5]=[CH:6][C:7]([CH:8]([O:13][CH2:14][O:15][CH3:16])[CH2:9][CH2:10][CH2:11][CH3:12])=[C:2]([F:1])[CH:3]=1)[CH:18]([CH3:20])[CH3:19])(=[O:24])[CH3:23]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 19010744HCID 19010744, compound

Product 1

HCID 53791239HCID 53791239, compoundYield 95.2%

Procedure

A mixture of 1-[3-fluoro-4-[1-(methoxymethoxy)pentyl]phenyl]-2-methylpropanol (104 mg), acetic anhydride (66 mg) and N,N-dimethylaminopyridine (2 mg) was stirred at room temperature for 1 hour. The mixture was poured into ice water and extracted with ethyl acetate. The organic layer was washed with water and brine, dried over magnesium sulfate and concentrated. The residue was chromatographed on silica gel column eluting with a mixture of hexane and ethyl acetate (85:15) to give 1-[3-fluoro-4-[1-(methoxymethoxy)pentyl]phenyl]-2-methylpropyl acetate (113 mg) as an oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was chromatographed on silica gel column
  6. washeluting with a mixture of hexane and ethyl acetate (85:15)

Sources & evidence

ORD record
ord-25b551a069814fd891c420a72013e56f
Source dataset
uspto-grants-1994_08
Patent number
US05334716

Reaction notes

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