Water → HCID 66777118, compound

HRID 2091109Notes

Reaction equation

[CH:1]1([C:7]([C:9]2[O:10][C:11]3[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][C:12]=3[C:13]=2[CH3:14])=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].CC1C=CC(S(O[CH:39]2[CH2:44][CH2:43][O:42][CH2:41][CH2:40]2)(=O)=O)=CC=1.O>CN(C)C=O>[CH:1]1([C:7]([C:9]2[O:10][C:11]3[CH:18]=[CH:17][C:16]([O:19][CH:39]4[CH2:44][CH2:43][O:42][CH2:41][CH2:40]4)=[CH:15][C:12]=3[C:13]=2[CH3:14])=[O:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

Conditions

Temperature: 80 °C

Procedure

Cyclohexyl(5-hydroxy-3-methyl-1-benzofuran-2-yl)methanone (5.2 g) synthesized in the above-mentioned (3) was dissolved in dimethylformamide (100 mL), and potassium phosphate (7.4 g) and tetrahydro-2H-pyran-4-yl 4-methylbenzenesulfonate (9.0 g) synthesized by the method of EP-A-1367058 were added to the mixture at room temperature, and the mixture was stirred at 80° C. overnight. The reaction mixture was allowed to cool to room temperature, water (150 mL) was added and the mixture was extracted with diethyl ether (100 mL×2). The extract was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:10, volume ratio) to give the title object compound (7.1 g, 99%) as a pale-yellow solid.

Workup

additionwere added to the mixture at room temperature
temperatureto cool to room temperature
extractionthe mixture was extracted with diethyl ether (100 mL×2)
concentrationThe extract was concentrated under reduced pressure
customthe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:10, volume ratio)

Sources & evidence

ORD record: ord-53c44db5d685408b99e9fd56ec2f15f8
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08436043B2

Reaction notes

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