Acetone → HCID 66682368, compound
Reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([C@H]2CC[C@H](C=O)CC2)=[C:6]([F:18])[C:5]=1[F:19])[CH3:2].C[C:21](C)=[O:22].CC(C)=[O:26].OS(O)(=O)=O.O=[Cr](=O)=O.C1(C)C=CC=CC=1>O>[CH2:1]([O:3][C:4]1([C:21]([OH:22])=[O:26])[CH2:9][CH2:8][CH2:7][C@@H:6]([F:18])[C@@H:5]1[F:19])[CH3:2]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 35 °C
Procedure
The compound (16) (10.0 g) and acetone (50 ml) were mixed and the mixture was stirred at 35° C. for 30 minutes. Jones reagent (8N) (4.7 ml) was added to the mixture in the temperature range of 30 to 40° C. and the mixture was stirred at 35° C. for 2 hours. After the reaction mixture had been cooled to 30° C., toluene (200 ml) and water (200 ml) were added to the mixture and mixed with it. The mixture was then allowed to stand until it had separated into two phases of organic and aqueous phases, and the extraction into an organic phase was carried out. The resulting organic phase was separated, and washed successively with water, an aqueous solution of sodium thiosulfate and water, and then dried over anhydrous magnesium sulfate, giving 4-ethoxy-2,3-difluoro-(trans-4-cyclohexyl)-carboxylic acid (31) (8.8 g). The yield based on the compound (16) was 83.1%.
Workup
- stirringthe mixture was stirred at 35° C. for 2 hours
- temperatureAfter the reaction mixture had been cooled to 30° C.
- additionmixed with it
- customhad separated into two phases of organic and aqueous phases
- extractionthe extraction into an organic phase
- customThe resulting organic phase was separated
- washwashed successively with water
- dry with materialan aqueous solution of sodium thiosulfate and water, and then dried over anhydrous magnesium sulfate
Sources & evidence
- ORD record
- ord-9f05251ccfd64ff88a89785820fc93ad
- Source dataset
- uspto-grants-2013_08
- Patent number
- US08501038B2
Reaction notes
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