Acetic Anhydride → 1-Methyl-4-oxo-5-(prop-2-yn-1-yl)cyclopent-2-en-1-yl acetate

HRID 1981049Notes

Reaction equation

HRID 1981049 reaction equation
[OH:1][C:2]1([CH3:11])[CH:6]=[CH:5][C:4](=[O:7])[CH:3]1[CH2:8][C:9]#[CH:10].[C:12](OC(=O)C)(=[O:14])[CH3:13]>>[C:12]([O:1][C:2]1([CH3:11])[CH:6]=[CH:5][C:4](=[O:7])[CH:3]1[CH2:8][C:9]#[CH:10])(=[O:14])[CH3:13]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 130367862-Propargyl-3-hydroxy-3-methyl-4-cyclopentenone

Product 1

HCID 135172641-Methyl-4-oxo-5-(prop-2-yn-1-yl)cyclopent-2-en-1-yl acetate

Procedure

Into the same flask as used in Example 1, 3-hydroxy-2-propargyl-3-methyl-4-cyclopentenone (30 g) and acetic anhydride (70 g) were charged, and the resultant mixture was stirred at 100° to 120° C. for 3 hours. After completion of the reaction, the reaction mixture was subjected to the same work-up as in Example 11, followed by purification to give 36.4 g of dl-3-acetoxy-2-propargyl-3-methyl-4-cyclopentenone. Yield, 95%. B.P., 82°-86° C./0.2-0.3 mmHg.

Workup

  1. additionwere charged
  2. customAfter completion of the reaction
  3. customfollowed by purification

Sources & evidence

ORD record
ord-555961faabf541c99407427347d99953
Source dataset
uspto-grants-1985_04
Patent number
US04511655

Reaction notes

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