Nitromethane → Ethyl 6,6,6-trifluoro-3-(nitromethyl)hexanoate
Reaction equation
[F:1][C:2]([F:13])([F:12])[CH2:3][CH2:4][CH:5]=[CH:6][C:7]([O:9][CH2:10][CH3:11])=[O:8].N12CCCN=C1CCCCC2.[N+:25]([CH3:28])([O-:27])=[O:26]>>[F:1][C:2]([F:12])([F:13])[CH2:3][CH2:4][CH:5]([CH2:28][N+:25]([O-:27])=[O:26])[CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8]Participants
4
Procedure
To ethyl 6,6,6-trifluorohex-2-enoate a6 (54.42 g, 0.277 mol, 1 eq) in nitromethane (250 ml) is added in one portion 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU, 41.5 ml, 0.277 mol, 1 eq). The reaction mixture is stirred at room temperature for 3 hours, then the nitromethane layer is washed two times a 2N HCl aqueous solution (250 ml). The cumulated aqueous layers are extracted by ethyl acetate (2×250 ml). The cumulated organic layers are dried over MgSO4, filtered and condensed under vacuum to yield 50 g of crude ethyl 6,6,6-trifluoro-3-(nitromethyl)hexanoate a7 which is used in the next step without any further purification.
Workup
- washthe nitromethane layer is washed two times a 2N HCl aqueous solution (250 ml)
- extractionThe cumulated aqueous layers are extracted by ethyl acetate (2×250 ml)
- dry with materialThe cumulated organic layers are dried over MgSO4
- filtrationfiltered
- customcondensed under vacuum
Sources & evidence
- ORD record
- ord-29d68a1eb56f48fdbd0e1c379cd2e6a7
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08822508B2
Reaction notes
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