Benzene → (E)-ethyl 7-hydroxy-2-methyl-2-heptenate

HRID 658959Notes

Reaction equation

HRID 658959 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[OH:7].C([O:10][C:11]([CH2:13][CH:14]=[C:15]1CCP(C2C=CC=CC=2)C1(C1C=CC=CC=1)C1C=CC=CC=1)=O)C.[CH:38]1C=CC=CC=1>>[OH:10][CH2:11][CH2:13][CH2:14][CH2:15]/[CH:4]=[C:3](\[CH3:38])/[C:2]([O:1][CH2:6][CH3:5])=[O:7]

Participants

4

Reactant 3

HCID 241BenzeneHCID 1365052-HydroxytetrahydropyranHCID 67123092(Ethoxycarbonylethylidene) triphenylphospholane

Product 1

HCID 10559469(E)-ethyl 7-hydroxy-2-methyl-2-heptenate

Conditions

Temperature
90 °C

Procedure

Tetrahydropyran-2-ol (2) (14.03 g; 0.138 mol) is added to a benzene solution (300 ml) of (ethoxycarbonylethylidene) triphenylphospholane (64.40 g; 0.178 mol) and the whole is refluxed at 90° C. for 1.5 hours. After the temperature is returned to room temperature, the solvent is then distilled off under reduced pressure, and the residue is separated and purified by column chromatography (developing solution, ethyl acetate:hexane=1:5) to produce Ester 3 (25.15 g; 0.135 mol) of 98% in yield.

Workup

  1. customis returned to room temperature
  2. distillationthe solvent is then distilled off under reduced pressure
  3. customthe residue is separated
  4. custompurified by column chromatography (developing solution, ethyl acetate:hexane=1:5)

Sources & evidence

ORD record
ord-983cda35bd42423d85c53cddada51a4d
Source dataset
uspto-grants-2011_12
Patent number
USRE043038E1

Reaction notes

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