Sodium Carbonate → 31753-17-0

HRID 428823Notes

Reaction equation

[Si]([O:8][CH:9]1[C@H:22]([CH:23]=[CH:24][CH:25]([OH:31])[CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[C@@H:12]([CH2:13][CH:14]=[CH:15][CH2:16][CH2:17][CH2:18][C:19]([O-:21])=[O:20])[C:11](=[O:32])[CH2:10]1)(C(C)(C)C)(C)C.F.[C:34](=O)([O-])[O-].[Na+].[Na+]>C(#N)C>[CH3:30][CH2:29][CH2:28][CH2:27][CH2:26][C@H:25]([OH:31])/[CH:24]=[CH:23]/[C@@H:22]1[C@@H:12]([CH2:13]/[CH:14]=[CH:15]/[CH2:16][CH2:17][CH2:18][C:19]([O:21][CH3:34])=[O:20])[C:11](=[O:32])[CH2:10][C@H:9]1[OH:8]

Participants

Conditions

Temperature: 0 °C

Procedure

(−)-methyl(11R, 15S, 5Z, 13E)-11-tert-butyldimethylsilyloxy-15-hydroxy-9-oxoprost-5,13-dien1-oate (518 mg, 1.08 mmol) and acetonitrile (10 ml) were placed into a Teflon container and cooled to 0° C., whereby 46% hydrofluoric acid (1.0 ml) was added and stirred for 2 h. The reaction mixture was poured into a saturated aqueous sodium carbonate cooled with ice and extracted with ethyl acetate (150 ml) two times. The combined organic layer was washed with a saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and concentrated in vacuo to remove solvent. The residue was purified by silica gel column chromatography [ethyl acetate/hexane (2/1)] to give 345 mg (88% yield) of prostaglandin E2 methyl ester;

Workup

temperaturecooled with ice
extractionextracted with ethyl acetate (150 ml) two times
washThe combined organic layer was washed with a saturated aqueous sodium chloride
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated in vacuo
customto remove solvent
customThe residue was purified by silica gel column chromatography [ethyl acetate/hexane (2/1)]

Sources & evidence

ORD record: ord-6ed0a1e8ebdb4ee2870e3838955290d8
Source dataset: uspto-grants-2001_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06313341B1

Reaction notes

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