Triethylamine → Ethyl(+/-)-4-(4,4,4-trifluoro-1-((methylsulfonyl)oxy)butyl)benzoate
Reaction equation
[F:1][C:2]([F:19])([F:18])[CH2:3][CH2:4][CH:5]([C:7]1[CH:17]=[CH:16][C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:9][CH:8]=1)[OH:6].C(N(CC)CC)C.[CH3:27][S:28](Cl)(=[O:30])=[O:29]>COC(C)(C)C>[F:1][C:2]([F:18])([F:19])[CH2:3][CH2:4][CH:5]([C:7]1[CH:17]=[CH:16][C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:9][CH:8]=1)[O:6][S:28]([CH3:27])(=[O:30])=[O:29]Participants
Procedure
To a solution of ethyl (+/−)-4-(4,4,4-trifluoro-1-hydroxybutyl)benzoate (264 mg, 0.956 mmol) in tert-butyl methyl ether (4.8 mL) was added triethylamine (0.201 mL, 1.43 mmol), followed by methanesulfonyl chloride (0.091 mL, 1.15 mmol). The resulting mixture was stirred for 1 hour. Then, the reaction mixture was diluted with tert-butyl methyl ether (25 mL) and washed with water (15 mL), sat. aq sodium bicarbonate (15 mL), then sat. aq sodium chloride (15 mL). The organic layer was dried over Na2SO4 and filtered, and the filtrate was concentrated under reduced pressure to give ethyl (+/−)-4-(4,4,4-trifluoro-1-((methylsulfonyl)oxy)butyl)benzoate. This material was used without further purification. 1HNMR (400 MHz, CDCl3) δ 8.12 (d, J=8.4 Hz, 2 H), 7.48 (d, J=8.2 Hz, 2 H), 5.63 (dd, J=7.9, 4.8 Hz, 1 H), 4.41 (q, J=7.0 Hz, 2 H), 2.77 (s, 3 H), 2.39-2.08 (m, 4 H), 1.41 (t, J=7.1 Hz, 3 H).
Workup
- washwashed with water (15 mL), sat. aq sodium bicarbonate (15 mL)
- dry with materialThe organic layer was dried over Na2SO4
- filtrationfiltered
- concentrationthe filtrate was concentrated under reduced pressure
Sources & evidence
- ORD record
- ord-5527d68c3e764e28a7d0ab9ec0717f17
- Source dataset
- uspto-grants-2015_09
- Patent number
- US09139538B2
Reaction notes
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