HCID 131718006, compound → methyl (Z)-7-{(1R)-(2R,5S)-2-(5,5-difluoro-4oxooctyl)-5-hydroxy-3-oxocylopentyl}hept-5-enoate

HRID 1588448Notes

Reaction equation

HRID 1588448 reaction equation
[F:1][C:2]([F:34])([CH2:31][CH2:32][CH3:33])[C:3](=[O:30])[CH2:4][CH2:5][CH2:6][C@H:7]1[C:11](=[O:12])[CH2:10][C@H:9]([O:13]C2CCCCO2)[C@@H:8]1[CH2:20]/[CH:21]=[CH:22]\[CH2:23][CH2:24][CH2:25][C:26]([O:28][CH3:29])=[O:27]>C(O)(=O)C.C1COCC1.O>[F:1][C:2]([F:34])([CH2:31][CH2:32][CH3:33])[C:3](=[O:30])[CH2:4][CH2:5][CH2:6][C@H:7]1[C:11](=[O:12])[CH2:10][C@H:9]([OH:13])[C@@H:8]1[CH2:20]/[CH:21]=[CH:22]\[CH2:23][CH2:24][CH2:25][C:26]([O:28][CH3:29])=[O:27]

Participants

5

Reactant 1

HCID 131718006HCID 131718006, compound

Product 1

HCID 15200568methyl (Z)-7-{(1R)-(2R,5S)-2-(5,5-difluoro-4oxooctyl)-5-hydroxy-3-oxocylopentyl}hept-5-enoate

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

The diketone (42) (0.188 g) was dissolved in a mixed solvent of acetic acid, THF and water (3:1:1, 25 ml) and the resultant mixture was kept at 40° C. for 3.5 hours. The crude product obtained after the usual work-up was subjected to silicagel column chromatography to give the titled compound (43).

Workup

  1. customThe crude product obtained after the usual work-up

Sources & evidence

ORD record
ord-6c6380588c694f2fa9d9eb972d5074c6
Source dataset
uspto-grants-1993_06
Patent number
US05221799

Reaction notes

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