Water → HCID 86622590, compound
Reaction equation
CN(CCN(C)C)C.[F:9][S:10]([F:23])([F:22])([F:21])([F:20])[C:11]1[CH:19]=[CH:18][C:14]([C:15]([OH:17])=[O:16])=[CH:13][CH:12]=1.[Cl:24]C(Cl)(Cl)C(Cl)(Cl)Cl.O>C1COCC1.[Li]C(CC)C.C1CCCCC1>[Cl:24][C:13]1[CH:12]=[C:11]([S:10]([F:20])([F:21])([F:22])([F:23])[F:9])[CH:19]=[CH:18][C:14]=1[C:15]([OH:17])=[O:16]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- -90 °C
Procedure
20.0 ml of TMEDA were dissolved in 150 ml of THF (anhydrous) and, at a temperature between −80° C. and −90° C., 93.0 ml of a 1.25M solution of sec-BuLi in cyclohexane were added. Then, at a temperature between −87° C. and −93° C., a solution of 4-pentafluorosulfanylbenzoic acid (example 2a) in 50 ml of THF (anhydrous) was added dropwise over the course of 35 minutes, After stirring at −90° C. for 2 hours, 38.2 g of 1,1,1,2,2,2-hexachloroethane in 60 ml of THF (anhydrous) were added dropwise at −90° C. The mixture was allowed to warm to −70° C., and then 100 ml of water were added dropwise. The solvent was removed in vacuo, and the residue was chromatographed on silica gel with DIP/2% HOAc. 5.0 g of the desired product were obtained as a partly crystallizing oil.
Workup
- additionwere added
- temperatureto warm to −70° C.
- customThe solvent was removed in vacuo
- customthe residue was chromatographed on silica gel with DIP/2% HOAc
Sources & evidence
- ORD record
- ord-868788d64c744ccdba8bc1f1c3004124
- Source dataset
- uspto-grants-2011_08
- Patent number
- US08008352B2
Reaction notes
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