Ethanol → 4-Pentynoic acid ethyl ester
Reaction equation
[C:1]([OH:7])(=[O:6])[CH2:2][CH2:3][C:4]#[CH:5].OS(O)(=O)=O.[CH2:13](O)[CH3:14]>>[C:1]([O:7][CH2:13][CH3:14])(=[O:6])[CH2:2][CH2:3][C:4]#[CH:5]Participants
4
Conditions
- Temperature
- 50 °C
Procedure
In analogy to the method as described in Tetrahedron, 2000, 56, 5735-5742, a mixture of the 4-pentynoic acid (10 g, 102 mmol) and H2SO4 98% (0.338 mL, 6.12 mmol) in ethanol (113 mL) was heated at 50° C. overnight. The reaction mixture was concentrated and the crude product was dissolved in ethyl acetate, washed with NaHCO3 1M and water. The solvent was removed under reduced pressure to afford 9.04 g of ethyl pent-4-ynoate (Yield: 70%) as a colorless oil.
Workup
- concentrationThe reaction mixture was concentrated
- dissolutionthe crude product was dissolved in ethyl acetate
- washwashed with NaHCO3 1M and water
- customThe solvent was removed under reduced pressure
Sources & evidence
- ORD record
- ord-5db63e7f35cd4adc911dba433aed20ec
- Source dataset
- uspto-grants-2014_11
- Patent number
- US08883826B2
Reaction notes
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