Trifluoroacetic anhydride → HCID 71272333, compound
Reaction equation
FC(F)(F)C(OC(=O)C(F)(F)F)=O.[CH3:14][O:15][CH2:16][CH:17]([OH:30])[CH2:18][C:19]1[N:23]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[N:22]=[CH:21][CH:20]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(N(CC)CC)C.C1COCC1.CS(C)=O>[CH3:14][O:15][CH2:16][C:17](=[O:30])[CH2:18][C:19]1[N:23]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[N:22]=[CH:21][CH:20]=1Participants
Conditions
- Temperature
- -42 °C
Procedure
To a THF solution (100 ml) of DMSO (14.2 ml) was added dropwise trifluoroacetic anhydride over 15 min at −42° C., and the mixture was stirred at −42° C. for 15 min. To the reaction mixture was added dropwise an THF solution (66 ml) of 1-methoxy-3-(1-phenyl-1H-pyrazol-5-yl)propan-2-ol (9.3 g) over 1 hr at −42° C., and the mixture was stirred at 0° C. for 15 min. To the reaction mixture was added dropwise triethylamine (22.3 ml) over 15 min at 0° C., and the mixture was stirred at 0° C. for 1 hr. To the reaction mixture was added 10% aqueous sodium carbonate solution, and the mixture was extracted with ethyl acetate, and the extract was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (4.11 g).
Workup
- stirringthe mixture was stirred at 0° C. for 15 min
- stirringthe mixture was stirred at 0° C. for 1 hr
- extractionthe mixture was extracted with ethyl acetate
- concentrationthe extract was concentrated under reduced pressure
- customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)
Sources & evidence
- ORD record
- ord-bbb2117a457e4ea9b9133d6f44c9b2ce
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09090586B2
Reaction notes
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