Trifluoroacetic acid → 3-(3-Cyclopentyloxy-4-methoxyphenyl)tetrahydrothiophene
Reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([C:15]3(O)[CH2:19][CH2:18][S:17][CH2:16]3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1.C([SiH](CC)CC)C.FC(F)(F)C(O)=O>ClCCl>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:15]3[CH2:19][CH2:18][S:17][CH2:16]3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1Participants
Procedure
A solution of 3-(3-cyclopentyloxy-4-methoxyphenyl)-3-hydroxytetrahydrothiophene (2.94 g; which is prepared as described in Example 14) and triethylsilane (2.7 mL) in dichloromethane (30 mL) under a nitrogen atmosphere is treated with trifluoroacetic acid (2.3 mL) during 15 minutes. The mixture is stirred for 3.5 hours and then it is allowed to stand for 2 days. The mixture is diluted with dichloromethane (150 mL) and the solution is washed with saturated aqueous sodium bicarbonate solution (2×25 mL), brine (2×25 mL) and water (2×25 mL). The solution is dried over magnesium sulphate, the solvent is removed and the oily residue is subjected to flash chromatography, using a mixture of pentane and ethyl acetate (19:1 v/v) as eluent, to give 3-(3-cyclopentyloxy-4-methoxyphenyl)tetrahydrothiophene (1.34 g) in the form of a pale yellow oil.
Workup
- waitto stand for 2 days
- washthe solution is washed with saturated aqueous sodium bicarbonate solution (2×25 mL), brine (2×25 mL) and water (2×25 mL)
- dry with materialThe solution is dried over magnesium sulphate
- customthe solvent is removed
- additiona mixture of pentane and ethyl acetate (19:1 v/v) as eluent
Sources & evidence
- ORD record
- ord-0965f0b5bf7e47df8b45dc2450c5c43e
- Source dataset
- uspto-grants-1996_07
- Patent number
- US05541219
Reaction notes
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