Acetic Acid → HCID 13681246, compound

HRID 365498Notes

Reaction equation

[CH2:1]1[CH2:11][C:9](=[O:10])[C:8]2[C:3](=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:2]1.C([N-]C(C)C)(C)C.[Li+].[P:20](Cl)([O:25][CH2:26][CH3:27])([O:22][CH2:23][CH3:24])=[O:21].C(O)(=O)C>C1COCC1.CCOCC>[O:10]=[C:9]1[C:8]2[C:3](=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:2][CH2:1][CH:11]1[P:20](=[O:21])([O:25][CH2:26][CH3:27])[O:22][CH2:23][CH3:24]

Participants

Conditions

Temperature: -65 °C

Procedure

A solution of α-tetralone (10 g, 68 mmol) in anhydrous THF (120 ml) is added dropwise to 1M lithium diisopropylamide solution (75 .mol, 75 ml) stirred at -65° C. under nitrogen. After stirring for 45 minutes, diethyl chlorophosphate (12.90 g, 75 mmol) is added to the enolate formed and the temperature of the mixture is progressively raised to 0° C. over a period of 50 minutes. After cooling to -70° C., the mixture is transferred to 2M lithium diisopropylamide solution (150 mmol, 75 ml). The solution obtained is stirred for 2 hours at 10° C. and then treated with acetic acid (272 mmol, 15.5 ml) in ether (250 ml). The mixture is filtered and the filtrate is concentrated. The title compound is obtained by purification on a flash column (eluant: cyclohexane/EtOAc=60/40).

Workup

stirringAfter stirring for 45 minutes
customformed
temperaturethe temperature of the mixture is progressively raised to 0° C. over a period of 50 minutes
temperatureAfter cooling to -70° C.
customThe solution obtained
stirringis stirred for 2 hours at 10° C.
filtrationThe mixture is filtered
concentrationthe filtrate is concentrated

Sources & evidence

ORD record: ord-075d809c38f44f529344faf89b36a2ba
Source dataset: uspto-grants-2000_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06127396

Reaction notes

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