Benzophenone → HCID 66624070, compound

HRID 420827Notes

Reaction equation

HRID 420827 reaction equation
[CH2:1]1[CH2:32][O:31][C:3]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])([CH2:4][CH2:5][C@H:6]2[CH:10]=[CH:9][C:8](=[O:11])[C@@H:7]2[CH2:12]/[CH:13]=[CH:14]\[CH2:15][CH2:16][CH2:17][C:18]([O:20][CH:21]([CH3:23])[CH3:22])=[O:19])[O:2]1.[C:33](C1C=CC=CC=1)(=[O:40])C1C=CC=CC=1>CO>[CH:21]([O:20][C:18](=[O:19])[CH2:17][CH2:16][CH2:15][CH:14]=[CH:13][CH2:12][C@H:7]1[C:8](=[O:11])[CH2:9][C@@H:10]([CH2:33][OH:40])[C@@H:6]1[CH2:5][CH2:4][C:3]1([O:2][CH2:1][CH2:32][O:31]1)[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])([CH3:22])[CH3:23]

Participants

4

Reactant 2

HCID 3102BenzophenoneHCID 12015883HCID 12015883, compound

Product 1

HCID 66624070HCID 66624070, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Isopropyl (Z)-7-[(1R,2S)-2-(3,3-ethylenedioxydecyl)-5-oxo-cyclopent-3-enyl]hept-5-enoate (3) (0.81 g) and benzophenone were dissolved in methanol. Under argon atmosphere, the solution was irradiated with 300-W high-pressure mercury lamp for 4 hours and 40 minutes. After evaporation of the solvent, the crude product was chromatographed on silica gel (n-hexane/ethyl acetate=3/2) to give isopropyl-7-[(1R,2S,3R)-2-(3,3-ethylenedioxydecyl)-3-hydroxymethyl-5-oxocyclopentyl]hept-5-enoate (4). Yield 0.41 g, 47%.

Workup

  1. customAfter evaporation of the solvent
  2. customthe crude product was chromatographed on silica gel (n-hexane/ethyl acetate=3/2)

Sources & evidence

ORD record
ord-7cb752b106ab4241b56f963dfb821913
Source dataset
uspto-grants-2012_01
Patent number
US08097649B1

Reaction notes

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