Ethanol → HCID 21693927, compound

Reaction equation

[CH2:1]([CH:7]1[CH:10](CC(OC2CCCCO2)CCCCCCCCCCC)[O:9][C:8]1=[O:31])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[NH+]1C=CC=CC=1.[C:38]1([CH3:48])[CH:43]=[CH:42][C:41](S([O-])(=O)=O)=[CH:40][CH:39]=1.C([OH:51])C>>[OH:51][CH:2]([CH2:3][CH2:4][CH2:5][CH2:6][CH2:48][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])[CH2:1][CH:7]1[CH2:10][O:9][C:8]1=[O:31]

Participants

Reactant 3

HCID 702Ethanol

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)

HCID 217639362-Oxetanone, 3-hexyl-4-[2-[(tetrahydro-2H-pyran-2-yl)oxy]tridecyl]-

Product 1

HCID 21693927HCID 21693927, compound

Procedure

(1B.a) 265 mg of an isomer mixture of 3-hexyl-4-[2-[(tetrahydro-2H-pyran-2-yl)oxy]tridecyl]-2-oxetanone are dissolved in 2.5 ml of ethanol and 13 mg of pyridinium-4-toluenesulphonate are added. The reaction mixture is heated to 55°-60° C. until the reaction has finished. The solvent is removed in vacuo and the residue is taken up in ether, whereby there separate crystals which are removed by filtration. The solvent is evaporated off in vacuo and the residue is chromatographed on silica gel. There is obtained rac-3-hexyl-4-(2-hydroxytridecyl-2-oxetanone (2R,3S,4S:2S, 3R,4R), MS: M+ (354), m.p. 44.5°-46° C.