Triphenylphosphine → {4-[3,3-Bis-(2-furanyl)-allylsulfanyl]-2-trifluoromethyl-phenoxy}-acetic acid ethyl ester
Reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([C:10]1[O:11][CH:12]=[CH:13][CH:14]=1)=[CH:7][CH2:8]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O.[CH2:46]([O:48][C:49](=[O:63])[CH2:50][O:51][C:52]1[CH:57]=[CH:56][C:55]([SH:58])=[CH:54][C:53]=1[C:59]([F:62])([F:61])[F:60])[CH3:47]>C1COCC1>[CH2:46]([O:48][C:49](=[O:63])[CH2:50][O:51][C:52]1[CH:57]=[CH:56][C:55]([S:58][CH2:8][CH:7]=[C:6]([C:10]2[O:11][CH:12]=[CH:13][CH:14]=2)[C:2]2[O:1][CH:5]=[CH:4][CH:3]=2)=[CH:54][C:53]=1[C:59]([F:60])([F:61])[F:62])[CH3:47]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 3,3-bis-(2-furanyl)-prop-2-en-1-ol (104 mg, 0.55 mmol) and triphenylphosphine (275 mg, 1.09 mmol) in THF (10 ml) was added, at room temperature and under nitrogen atmosphere, DEAD (190 mg, 1.09 mmol). The reaction mixture was stirred for 5 min after which (2-trifluoromethyl4-mercapto-phenoxy)-acetic acid ethyl ester (230 mg, 0.82 mmol) was added over 15 min. The reaction mixture was stirred at 0oC for 2 hours followed by 18 hours at room temperature and 3 hours at 50° C. The reaction mixture was evaporated and the crude residue was purified on column chromatography using ethyl acetate as eluent. The desired {4-[3,3-bis-(2-furanyl)-allylsulfanyl]-2-trifluoromethyl-phenoxy}-acetic acid ethyl ester was isolated in 11 mg yield.
Workup
- additionwas added over 15 min
- waitfollowed by 18 hours at room temperature and 3 hours at 50° C
- customThe reaction mixture was evaporated
- customthe crude residue was purified on column chromatography
Sources & evidence
- ORD record
- ord-f424a99be8ed4ead94c7c10705857c11
- Source dataset
- uspto-grants-2006_10
- Patent number
- US07129268B2
Reaction notes
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