2-Phenylethanol → Methyl 7-(2-oxocyclopentyl)heptanoate

HRID 1973165Notes

Reaction equation

HRID 1973165 reaction equation
[O:1]=[C:2]1[C:6]([CH2:7]/[CH:8]=[CH:9]\[CH2:10][CH2:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])=[CH:5][CH2:4][CH2:3]1.C1(CCO)C=CC=CC=1.[H][H]>[Rh]Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[O:1]=[C:2]1[CH:6]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])[CH2:5][CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 60542-PhenylethanolHCID 690371607-(5-Oxo-1-cyclopentenyl)-cis-5-heptenoic acid, methyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 13099223Methyl 7-(2-oxocyclopentyl)heptanoate

Reagents, catalysts & solvents 1

HCID 178479813HCID 178479813, compoundCatalyst

Procedure

A solution of 8.8 g. of 7-(5-oxo-1-cyclopentenyl)-cis-5-heptenoic acid, methyl ester and 6.6 g. of tris-(triphenylphosphine) rhodium (I) chloride in 800 ml. of 1:1 benzene-ethanol is hydrogenated at 25° and atmospheric pressure until 1 equivalent of hydrogen was absorbed. The solvents are evaporated and the resulting residue dissolved in 1:1 ethyl acetate-hexane and flushed through a silica column. The crude product is then rechromatographed on silica with 15% ethyl acetate in hexane to obtain 7.2 g. of the title product as an oil.

Workup

  1. customis hydrogenated at 25°
  2. customThe solvents are evaporated
  3. dissolutionthe resulting residue dissolved in 1:1 ethyl acetate-hexane
  4. customflushed through a silica column
  5. customThe crude product is then rechromatographed on silica with 15% ethyl acetate in hexane
  6. customto obtain 7.2 g

Sources & evidence

ORD record
ord-cf425e4f103c417a9966bd9d12a39062
Source dataset
uspto-grants-1976_12
Patent number
US03996255

Reaction notes

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