2,2-dimethyl-4-{4-[(phenylmethyl)oxy]-1-buten-1-yl}tetrahydro-2H-pyran → 4-(2,2-Dimethyltetrahydro-2H-pyran-4-yl)-1-butanol
Reaction equation
[CH3:1][C:2]1([CH3:20])[CH2:7][CH:6]([CH:8]=[CH:9][CH2:10][CH2:11][O:12]CC2C=CC=CC=2)[CH2:5][CH2:4][O:3]1>[Pd].C(OCC)(=O)C>[CH3:1][C:2]1([CH3:20])[CH2:7][CH:6]([CH2:8][CH2:9][CH2:10][CH2:11][OH:12])[CH2:5][CH2:4][O:3]1Participants
4
Procedure
A solution of 2,2-dimethyl-4-{4-[(phenylmethyl)oxy]-1-buten-1-yl}tetrahydro-2H-pyran (7.46 g, 27.2 mmol) I ethyl acetate (70 ml) was hydrogenated over 10% palladium on activated carbon (1.447 g, 1.359 mmol) at atmospheric pressure and room temperature. After 16 hours, the mixture was filtered under vacuum through Celite, washed through with EtOAc (2×50 ml) and the filtrate was evaporated to dryness to give a yellowish mobile oil (4.8 g). The residue was purified by chromatography on silica (70 g) using a cyclohexane:ethyl acetate 0->50% gradient over 40 mins using a Flashmaster II. The desired fractions (analysed with a permanganate dip) were combined and concentrated under vacuum to give the title compound as a yellow oil (1.675 g).