Acetic Anhydride → HCID 15723371, compound

HRID 654914Notes

Reaction equation

HRID 654914 reaction equation
[OH:1][CH:2]([C:12]1[CH:13]=[C:14]([Si:17]([CH3:20])([CH3:19])[CH3:18])[O:15][CH:16]=1)[CH2:3][CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[C:21](OC(=O)C)(=[O:23])[CH3:22]>N1C=CC=CC=1>[C:21]([O:1][CH:2]([C:12]1[CH:13]=[C:14]([Si:17]([CH3:20])([CH3:19])[CH3:18])[O:15][CH:16]=1)[CH2:3][CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)(=[O:23])[CH3:22]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 19885953HCID 19885953, compound

Product 1

HCID 15723371HCID 15723371, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineCatalyst

Procedure

A solution of 4-(1-hydroxy-4-phenylbutyl)-2-trimethylsilylfuran (0.249 g., 0.862 mmol), acetic anhydride (1 ml, excess) and pyridine (3 to 4 drops, excess) was stirred at room temperature until no starting material remained (as monitored by TLC). The reaction mixture was then partitioned between ethyl ether and a 5% ammonium chloride solution. The organic portion was washed repeatedly with saturated sodium bicarbonate solution, twice with aqueous cupric sulfate solution, water, saturated sodium chloride solution, dried over magnesium sulfate, filtered and concentrated to give a pale yellow oil (0.396 g). This material was further purified by flash chromatography (silica, 5% ethyl acetate/hexane) to give the desired acetate.

Workup

  1. customThe reaction mixture was then partitioned between ethyl ether
  2. washThe organic portion was washed repeatedly with saturated sodium bicarbonate solution, twice with aqueous cupric sulfate solution, water, saturated sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-58dd659746294c1c96c31a140fac7d4e
Source dataset
uspto-grants-1992_07
Patent number
US05134128

Reaction notes

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