Propargyl alcohol → Prop-2-ynyl 3-oxopentanoate

HRID 1471327Notes

Reaction equation

HRID 1471327 reaction equation
[OH:1][C:2](=[C:5]1[C:10](=[O:11])[O:9][C:8]([CH3:13])(C)OC1=O)[CH2:3][CH3:4].[CH2:15](O)C#C>C1C=CC=CC=1>[O:1]=[C:2]([CH2:3][CH3:4])[CH2:5][C:10]([O:9][CH2:8][C:13]#[CH:15])=[O:11]

Participants

4

Reactant 2

HCID 7859Propargyl alcoholHCID 547061775-(1-Hydroxypropylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione

Product 1

HCID 58512883Prop-2-ynyl 3-oxopentanoateYield 95.4%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Method A. A solution of 5-(1-hydroxypropylidene)-2,2-dimethyl-[1,3]dioxane-4,6-dione (2) (2.00 g, 10.0 mmol) and 2-propynol (1.10 g, 20.0 mmol) in benzene (20 mL) is stirred at 93° C. for 3.25 h and then cooled to room temperature. After solvent removal at reduced pressure, the residue is purified on silica gel (12.5% to 14.3% ethyl acetate/hexane) to give 1.47 g (95%) of 4 as a colorless liquid.

Workup

  1. customAfter solvent removal at reduced pressure
  2. customthe residue is purified on silica gel (12.5% to 14.3% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-d38a9d9a4391433ebd62d31adb618839
Source dataset
uspto-grants-2015_04
Patent number
US09012217B2

Reaction notes

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