Sodium Sulfite → HCID 44232353, compound

HRID 1799807Notes

Reaction equation

HRID 1799807 reaction equation
[C:1]([C:3]([C:19]#[N:20])([CH2:13][CH2:14][C:15]([F:18])([F:17])[F:16])[CH2:4][CH:5]1[CH2:10][CH2:9][C:8]([C:11]#[CH:12])=[CH:7][CH2:6]1)#[N:2].ClC1C=CC=C(C(OO)=[O:29])C=1.S([O-])([O-])=O.[Na+].[Na+]>C(Cl)(Cl)Cl>[C:1]([C:3]([C:19]#[N:20])([CH2:13][CH2:14][C:15]([F:18])([F:17])[F:16])[CH2:4][CH:5]1[CH2:10][CH2:9][C:8]2([O:29][CH:7]2[CH2:6]1)[C:11]#[CH:12])#[N:2]

Participants

5

Reactant 3

HCID 24437Sodium SulfiteHCID 70297m-Chloroperbenzoic acidHCID 86650337HCID 86650337, compound

Product 1

HCID 44232353HCID 44232353, compoundYield 67.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 0.31 g of 4-(2,2-dicyano-5,5,5-trifluoropentyl)-1-ethynylcyclohexene in 3 mL of chloroform was added 0.23 g of m-chloroperbenzoic acid at 0° C., followed by stirring at room temperature for 5 hours. After the reaction mixture was cooled to 0° C., 5 mL of a 10% aqueous sodium sulfite solution was added thereto, followed by extraction twice with 30 mL of chloroform. The combined organic layer was washed sequentially with 30 mL of a 10% aqueous sodium sulfite solution, 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 0.22 g of 4-(2,2-dicyano-5,5,5-trifluoropentyl)-1,2-epoxy-1-ethynylcyclohexane (hereinafter referred to as the present compound (4)) represented by the following formula:

Workup

  1. temperatureAfter the reaction mixture was cooled to 0° C.
  2. extractionfollowed by extraction twice with 30 mL of chloroform
  3. washThe combined organic layer was washed sequentially with 30 mL of a 10% aqueous sodium sulfite solution, 30 mL of a saturated aqueous sodium hydrogen carbonate solution and 30 mL of a saturated aqueous sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-096e1d5efdac4f68a2beebc0037e08d2
Source dataset
uspto-grants-2013_01
Patent number
US08344163B2

Reaction notes

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