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

HRID 1433236Notes

Reaction equation

HRID 1433236 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-8e7b9e4d23c445d28adf2736c0f1a1ef
Source dataset
uspto-grants-2009_11
Patent number
US07612213B2

Reaction notes

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