Hydrochloric Acid → HCID 44232484, compound
Reaction equation
[C:1]([C:3]([C:19]#[N:20])([CH2:13][CH2:14][C:15]([F:18])([F:17])[F:16])[CH2:4][CH2:5][CH:6]1[CH2:11][CH2:10][C:9](=[O:12])[CH2:8][CH2:7]1)#[N:2].[C:21]([Mg]Br)#[CH:22].Cl>O1CCCC1>[C:1]([C:3]([C:19]#[N:20])([CH2:13][CH2:14][C:15]([F:18])([F:17])[F:16])[CH2:4][CH2:5][CH:6]1[CH2:7][CH2:8][C:9]([C:21]#[CH:22])([OH:12])[CH2:10][CH2:11]1)#[N:2]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 1.14 g of 4-(3,3-dicyano-6,6,6-trifluorohexyl)cyclohexanone in 10 mL of tetrahydrofuran was added 10 mL of a 0.5 M solution of ethynyl magnesium bromide in tetrahydrofuran at 0° C. under a nitrogen atmosphere, followed by stirring at 0° C. for 5 hours. To the reaction mixture was added 30 mL of a 1 N aqueous hydrochloric acid solution, followed by extraction twice with 30 mL of ethyl acetate. The combined organic layer was washed sequentially with 30 mL of a saturated aqueous sodium hydrogen carbonate solution and 30 mL of a saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered, and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 0.78 g of 1-(3,3-dicyano-6,6,6-trifluorohexyl)-4-ethynyl-4-hydroxycyclohexane (hereinafter referred to as the present compound (6)) represented by the following formula:
Workup
- extractionfollowed by extraction twice with 30 mL of ethyl acetate
- washThe combined organic layer was washed sequentially with 30 mL of a saturated aqueous sodium hydrogen carbonate solution and 30 mL of a saturated aqueous sodium chloride solution
- dry with materialdried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-4bdd5ca70cf149a3a5e3a5743e946647
- Source dataset
- uspto-grants-2013_01
- Patent number
- US08344163B2
Reaction notes
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