Tetrahydrofuran → HCID 131728904, compound

HRID 551648Notes

Reaction equation

O1CCCC1.COP([CH2:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])(OC)=O.[H-].[Na+].[CH:22]([C:26]1[CH2:27][C@@H:28]2[C@H:31]([CH:32]=1)[C:30](=O)[CH2:29]2)([CH2:24][CH3:25])[CH3:23]>O>[CH:22]([C:26]1[CH2:32][C@@H:31]2[C@H:28]([CH:27]=1)[C:29](=[CH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:30]2)([CH2:24][CH3:25])[CH3:23]

Participants

Conditions

Temperature: 0 °C

Procedure

A tetrahydrofuran (15 mL) solution of tert-butyl dimethylphosphonoacetate (3.70 g, 16.5 mmol) was added dropwise at 0° C. over 20 minutes to a tetrahydrofuran (15 mL) suspension of sodium hydride (0.68 g, 63%, 18.0 mmol), and the mixture was stirred at 0° C. for 20 minutes. To this solution, a tetrahydrofuran (15 mL) solution of (±)-(1S,5R)-3-sec-butylbicyclo[3.2.0]hept-3-en-6-one (2.48 g, 15.1 mmol) was added dropwise at 0° C. over 15 minutes, and the mixture was stirred at room temperature for 2 hours. The mixture was treated with water, followed by extraction with diethyl ether. The organic layer was dried over anhydrous magnesium sulfate. Then, the solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography to obtain the compound of interest as a yellow oil substance (3.10 g, 78%).

Workup

stirringthe mixture was stirred at room temperature for 2 hours
extractionfollowed by extraction with diethyl ether
dry with materialThe organic layer was dried over anhydrous magnesium sulfate
distillationThen, the solvent was distilled off under reduced pressure
customthe residue was purified by silica gel column chromatography
customto obtain the compound of interest as a yellow oil substance (3.10 g, 78%)

Sources & evidence

ORD record: ord-1567572fbedb4d51bdef597d03a821dc
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07947738B2

Reaction notes

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