Dicyclohexylcarbodiimide → (S,S)-[4-(2-fluorooctanoyloxy)-biphenyl-4'-yl] 4-(2-fluorooctyloxy)benzoate
Reaction equation
[F:1][C@@H:2]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[C:3]([O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=2)=[CH:8][CH:7]=1)=[O:4].C(OC1C=CC(C2C=CC(O)=CC=2)=CC=1)(=O)C1C=CC=CC=1.F[C@@H](CCCCCC)C(Cl)=O.[F:58][C@@H:59]([CH2:71][CH2:72][CH2:73][CH2:74][CH2:75][CH3:76])[CH2:60][O:61][C:62]1[CH:70]=[CH:69][C:65]([C:66](O)=[O:67])=[CH:64][CH:63]=1.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.ClCCl.N1C=CC=CC=1>[F:58][C@@H:59]([CH2:71][CH2:72][CH2:73][CH2:74][CH2:75][CH3:76])[CH2:60][O:61][C:62]1[CH:70]=[CH:69][C:65]([C:66]([O:18][C:15]2[CH:16]=[CH:17][C:12]([C:9]3[CH:8]=[CH:7][C:6]([O:5][C:3](=[O:4])[C@@H:2]([F:1])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[CH:11][CH:10]=3)=[CH:13][CH:14]=2)=[O:67])=[CH:64][CH:63]=1Participants
9
Reactant 5
Product 1
Reagents, catalysts & solvents 3
Procedure
0.02 mol of (S)-4-(2-fluorooctanoyloxy)-4'-hydroxybiphenyl (prepared by reaction of 4-benzoyloxy-4'-hydroxybiphenyl with (S)-2-fluorooctanoyl chloride in the presence of pyridine and subsequent removal of the benzyl group with hydrogenation), 0.02 mol of (S)-4-(2-fluorooctyloxy)benzoic acid and 0.002 mol of 4-dimethylaminopyridine are introduced into 30 ml of dichloromethane, a solution of 0.02 mol of dicyclohexylcarbodiimide is added dropwise at 10°with stirring, and the mixture is subsequently stirred at room temperature for a further 15 hours. Work-up gives (S,S)-[4-(2-fluorooctanoyloxy)-biphenyl-4'-yl] 4-(2-fluorooctyloxy)benzoate.
Workup
- stirringthe mixture is subsequently stirred at room temperature for a further 15 hours
Sources & evidence
- ORD record
- ord-2ead8ef3a95242769766fc2e972e5b30
- Source dataset
- uspto-grants-1995_02
- Patent number
- US05393459
Reaction notes
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