Trifluoroacetic acid methylene chloride → HCID 69134812, compound
Reaction equation
C(O[CH2:6][CH2:7][O:8][CH:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1)(C)(C)C.C(Cl)Cl.[F:18][C:19]([F:24])([F:23])[C:20]([OH:22])=[O:21]>>[F:18][C:19]([F:24])([F:23])[C:20]([O:22][CH2:6][CH2:7][O:8][CH:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1)=[O:21]Participants
Procedure
4-(2-tert-Butoxyethoxy)tetrahydropyran (24 g, 0.12 mol) was stirred in a mixture of methylene chloride/trifluoroacetic acid (150 ml/150 ml) at ambient temperature overnight. The solvents were evaporated off and the residual trifluoroacetic acid was azeotroped off with, toluene. The crude oil was purified by flash chromatography using successively petroleum ether, petroleum ether/methylene chloride (1/1) and methylene chloride. The organic phase was washed with water, brine, dried (MgSO4), filtered and the solvent evaporated. Evaporation of the solvent gave 4-(2-trifluoroacetoxyethoxy)tetrahydropyran which was hydrolysed with potassium hydrogen carbonate (48 g, 0.48 mol) in methanol (700 ml) and water (300 ml) at ambient temperature for 3 hours. The solution was neutralised to pH 7 and the solvents evaporated off. The residue was extracted with ethyl acetate, the organic phase washed with water and brine, dried (MgSO4) and the solvent evaporated off to give 4-(2-hydroxyethoxy)tetrahydropyran (6 g, 35%) as a light brown oil.
Workup
- customThe solvents were evaporated off
- customthe residual trifluoroacetic acid was azeotroped off with, toluene
- customThe crude oil was purified by flash chromatography
- washThe organic phase was washed with water, brine
- dry with materialdried (MgSO4)
- filtrationfiltered
- customthe solvent evaporated
- customEvaporation of the solvent
Sources & evidence
- ORD record
- ord-f4df2c5f151545ef9777da2c507ea102
- Source dataset
- uspto-grants-2008_05
- Patent number
- US07371765B2
Reaction notes
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