Hydrochloric Acid → 3,3-Difluoro-2-trifluoromethyl-2,3,3a,4,5,6,7,7a-octahydrobenzofuran-2,3a-diol
Reaction equation
C([Li])CCC.[F:6][C:7]([F:15])([F:14])[CH:8]([OH:13])[C:9](F)([F:11])[F:10].Cl[CH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][C:18]1=[O:23].Cl.[OH-:25].[Na+]>CCCCCC.O1CCCC1>[F:10][C:9]1([F:11])[C:18]2([OH:23])[CH2:19][CH2:20][CH2:21][CH2:22][CH:17]2[O:13][C:8]1([C:7]([F:15])([F:14])[F:6])[OH:25]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 5 °C
Procedure
In a nitrogen atmosphere at −5° C., 1000 ml of 2.6M n-butyllithium in hexane was added to a mixture of 224 g of 1,1,1,3,3,3-hexafluoro-2-propanol and 1000 g of tetrahydrofuran, followed by one hour of stirring at 5° C. Then 164 g of 2-chlorocyclohexanone was added at 5° C. The mixture was stirred for 10 hours, after which dilute hydrochloric acid was added to quench the reaction and neutralize the reaction mixture. Then 1200 g of a 10% aqueous solution of sodium hydroxide was added to the reaction mixture, from which an aqueous layer was separated. It was made acidic by adding 560 g of 20% dilute hydrochloric acid and combined with 1000 g of toluene, after which an organic layer was separated. The organic layer thus separated was concentrated and purified by recrystallization from hexane, obtaining 201 g of the product (yield 63%).
Workup
- stirringThe mixture was stirred for 10 hours
- customto quench
- customthe reaction
- customwas separated
- additionby adding 560 g of 20% dilute hydrochloric acid
- customafter which an organic layer was separated
- customThe organic layer thus separated
- concentrationwas concentrated
- custompurified by recrystallization from hexane
Sources & evidence
- ORD record
- ord-bed9d92fbbb3479e8304b2c1ae7d3bf8
- Source dataset
- uspto-grants-2009_05
- Patent number
- US07531289B2
Reaction notes
Loading…