Selectfluor → HCID 178501073, compound
Reaction equation
[CH3:1][O:2][C:3]([C@H:5]1[CH2:10][CH2:9][C@H:8]([C:11]2[CH:15]=[C:14]([CH3:16])[O:13][N:12]=2)[CH2:7][CH2:6]1)=[O:4].[B-](F)(F)(F)[F:18].[B-](F)(F)(F)F.C1[N+]2(CCl)CC[N+](F)(CC2)C1>C(#N)C>[CH3:1][O:2][C:3]([C@H:5]1[CH2:6][CH2:7][C@H:8]([C:11]2[C:15]([F:18])=[C:14]([CH3:16])[O:13][N:12]=2)[CH2:9][CH2:10]1)=[O:4]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
A mixture of trans-4-(5-methyl-isoxazol-3-yl)-cyclohexanecarboxylic acid methyl ester (250 mg, 1.12 mmol) and Selectfluor® (476 mg, 1.34 mmol) in acetonitrile (5.6 ml) was heated at 90° C. for 20 h. After cooling to room temperature the reaction mixture was partitioned between ethyl acetate (50 ml) and water (25 ml). The layers were separated. The aqueous layer was extracted with two 50 ml-portions of ethyl acetate. The combined organic layers were washed with one 25 ml-portion of water/brine (1:1), dried over anhydrous sodium sulfate and concentrated in vacuo. Purification with n-heptane/tert-butyl methyl ether as eluent gave the title compound (35 mg, 13%) as light yellow oil. MS m/e: 241 ([M+H]+)
Workup
- temperatureAfter cooling to room temperature the reaction mixture
- customwas partitioned between ethyl acetate (50 ml) and water (25 ml)
- customThe layers were separated
- extractionThe aqueous layer was extracted with two 50 ml-portions of ethyl acetate
- washThe combined organic layers were washed with one 25 ml-portion of water/brine (1:1)
- dry with materialdried over anhydrous sodium sulfate
- concentrationconcentrated in vacuo
- customPurification with n-heptane/tert-butyl methyl ether as eluent
Sources & evidence
- ORD record
- ord-0d7f73e78baa4e548525d8dc64ab37eb
- Source dataset
- uspto-grants-2013_08
- Patent number
- US08513238B2
Reaction notes
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