2,2,2-Trichloroethyl butyrate → 4-(Tetrahydropyran-2-yloxy)phenylethanol

HRID 344795Notes

Reaction equation

[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]([OH:16])[CH3:15])=[CH:10][CH:9]=1.[C:17](OCC(Cl)(Cl)Cl)(=[O:21])[CH2:18][CH2:19][CH3:20]>C(OCC)C>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]([OH:16])[CH3:15])=[CH:10][CH:9]=1.[C:17]([O:16][CH:14]([C:11]1[CH:12]=[CH:13][C:8]([O:7][CH:2]2[CH2:3][CH2:4][CH2:5][CH2:6][O:1]2)=[CH:9][CH:10]=1)[CH3:15])(=[O:21])[CH2:18][CH2:19][CH3:20]

Participants

Conditions

Temperature: 25 °C

Procedure

To 120 ml of anhydrous diethyl ether was added 22.2 g (0.1 mole) of 1-(4-(tetrahydro-2-pyranyloxy)phenyl)ethanol, 22.4 g (0.1 mole) of 2,2,2-trichloroethyl butyrate and 25.2 g of Lipase P, and the mixture was reacted with stirring at 25° C. for 90 hours. After the reaction mixture was filtered by suction to remove Lipase P, the filtrate was concentrated, and the concentrate was then purified by silica gel chromatography [ethyl acetate/n-hexane=1/4 by volume] to give 10.2 g of S-form of 1-(4-(tetrahydro-2-pyranyloxy)phenyl)ethanol (yield: 92%) and 13.1 g of R-form of 1-(4-(tetrahydro-2-pyranyloxy)phenyl)ethyl butyrate (yield: 91%).

Workup

customthe mixture was reacted
filtrationAfter the reaction mixture was filtered by suction
customto remove Lipase P
concentrationthe filtrate was concentrated
customthe concentrate was then purified by silica gel chromatography [ethyl acetate/n-hexane=1/4 by volume]

Sources & evidence

ORD record: ord-bc472212bb484b7da45df483971251dc
Source dataset: uspto-grants-1991_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05053507

Reaction notes

Loading…