Ethyl Acetate → 7-Hydroxy-hept-2-enoic acid ethyl ester

HRID 1515731Notes

Reaction equation

HRID 1515731 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][CH2:5][CH2:4]O1.[CH2:8]([O:10][C:11](=[O:13])[CH3:12])[CH3:9]>O1CCCC1>[CH2:8]([O:10][C:11](=[O:13])[CH:12]=[CH:4][CH2:5][CH2:6][CH2:7][CH2:2][OH:1])[CH3:9]

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 1365052-Hydroxytetrahydropyran

Product 1

HCID 713313427-Hydroxy-hept-2-enoic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2-hydroxytetrahydropyran (59.2 g, 0.58 mol) and triphenyl-λ5-phosphanylidene)-acetic acid ethyl ester (201.3 g, 0.58 mol) in tetrahydrofuran (1.2 L) was heated at reflux for 14 h. The mixture was cooled to room temperature to afford 7-hydroxy-hept-2-enoic acid ethyl ester in tetrahydrofuran and was then used directly in the next step.

Workup

  1. temperatureat reflux for 14 h

Sources & evidence

ORD record
ord-fafbc42bb7a64f7ab1388f63b65eef0c
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

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