Acetic Anhydride → HCID 22069773, compound

HRID 1757262Notes

Reaction equation

HRID 1757262 reaction equation
[CH3:1][C:2]([CH3:29])([CH3:28])[C:3]#[C:4]/[CH:5]=[CH:6]/[CH2:7]/[C:8](=[CH:11]\[CH2:12][CH2:13][CH2:14][CH2:15][O:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([C:23]2[CH:27]=[CH:26][S:25][CH:24]=2)[CH:18]=1)/[CH2:9][OH:10].[C:30](OC(=O)C)(=[O:32])[CH3:31]>N1C=CC=CC=1>[C:30]([O:10][CH2:9]/[C:8](/[CH2:7]/[CH:6]=[CH:5]/[C:4]#[C:3][C:2]([CH3:29])([CH3:28])[CH3:1])=[CH:11]/[CH2:12][CH2:13][CH2:14][CH2:15][O:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([C:23]2[CH:27]=[CH:26][S:25][CH:24]=2)[CH:18]=1)(=[O:32])[CH3:31]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 15288595HCID 15288595, compound

Product 1

HCID 22069773HCID 22069773, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

18.8 mg of (E,E)-2-(6,6-dimethyl-2-hepten-4-ynyl)-7-[3-(3-thienyl)phenoxy]-2-hepten-1-ol obtained in Example 2 is dissolved in 2 ml of pyridine, 1 ml of acetic anhydride is added, and the mixture is stirred at room temperature for 18 hours. The reaction solution is concentrated under reduced pressure, water and ethyl acetate are added to the residue for extraction, the organic layer is taken, washed successively with 1N hydrochloric acid, saturated aqueous sodium bicarbonate solution and saturated saline and dried over anhydrous magnesium sulfate, and the solvent is distilled off under reduced pressure. The residue is purified by preparative thin layer chromatography [Kieselgel 60 F254, Art. 5717 (produced by Merck Co.); hexane/ethyl acetate=5/1] to obtain 18.8 mg (yield: 91%) of the captioned compound as a colorless oily matter.

Workup

  1. concentrationThe reaction solution is concentrated under reduced pressure, water and ethyl acetate
  2. additionare added to the residue for extraction
  3. washwashed successively with 1N hydrochloric acid, saturated aqueous sodium bicarbonate solution and saturated saline
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent is distilled off under reduced pressure
  6. customThe residue is purified by preparative thin layer chromatography [Kieselgel 60 F254, Art. 5717 (produced by Merck Co.); hexane/ethyl acetate=5/1]

Sources & evidence

ORD record
ord-3c3662b070fd4453a8fe7e6ead2b3930
Source dataset
uspto-grants-1995_08
Patent number
US05444084

Reaction notes

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