Hydrochloric Acid → 2H-Pyran, tetrahydro-2-[4-(trifluoromethyl)phenoxy]-
Reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1.[O:12]1[CH:17]=[CH:16][CH2:15][CH2:14][CH2:13]1.Cl>ClCCl.C(OCC)(=O)C>[F:1][C:2]([F:10])([F:11])[C:3]1[CH:4]=[CH:5][C:6]([O:9][CH:13]2[CH2:14][CH2:15][CH2:16][CH2:17][O:12]2)=[CH:7][CH:8]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Procedure
a solution of 4-(trifluoromethyl)phenol (2.44 g, 15 mmol) in dichloromethane (5 ml) was added to a solution of 3,4-dihydro-2H-pyran (4.10 ml, 45 mmol) and a 3.6 M solution of hydrogen chloride in ethyl acetate (0.015 ml, 0.05 mmol) in dichloromethane (10 ml). The reaction mixture was stirred at room temperature for 16 h. It was diluted with ethyl acetate (100 m) and washed with a saturated aqueous solution of sodium hydrogencarbonate (100 ml). The aqueous phase was extracted with ethyl acetate (2×30 ml). The combined organic layers were dried over magnesium sulphate. The solvent was removed in vacuo. The crud product was purified by flash chromatography on silica (90 g), using ethyl acetate/heptane 1:10 as eluent to give 3.09 g of 2-(4-(trifluoromethyl)phenoxy)tetrahydropyran.
Workup
- washwashed with a saturated aqueous solution of sodium hydrogencarbonate (100 ml)
- extractionThe aqueous phase was extracted with ethyl acetate (2×30 ml)
- dry with materialThe combined organic layers were dried over magnesium sulphate
- customThe solvent was removed in vacuo
- customThe crud product was purified by flash chromatography on silica (90 g)
Sources & evidence
- ORD record
- ord-34389f6692d5408f94383c27fde01d5c
- Source dataset
- uspto-grants-2006_09
- Patent number
- US07101898B2
Reaction notes
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