Sodium Sulfite → HCID 86639421, compound

HRID 1690188Notes

Reaction equation

HRID 1690188 reaction equation
[CH2:1]([C:4]1[CH:20]=[C:19]([C:21]([O:30][CH2:31][O:32][CH3:33])([C:26]([F:29])([F:28])[F:27])[C:22]([F:25])([F:24])[F:23])[CH:18]=[CH:17][C:5]=1[O:6][C:7]1[CH:8]=[CH:9][C:10]([CH:15]=[CH2:16])=[C:11]([CH:14]=1)[C:12]#[N:13])[CH2:2][CH3:3].C(=O)([O-])[OH:35].[Na+].ClC1C=C(C=CC=1)C(OO)=O.S([O-])([O-])=O.[Na+].[Na+]>ClCCl>[O:35]1[CH2:16][CH:15]1[C:10]1[CH:9]=[CH:8][C:7]([O:6][C:5]2[CH:17]=[CH:18][C:19]([C:21]([O:30][CH2:31][O:32][CH3:33])([C:22]([F:23])([F:24])[F:25])[C:26]([F:28])([F:27])[F:29])=[CH:20][C:4]=2[CH2:1][CH2:2][CH3:3])=[CH:14][C:11]=1[C:12]#[N:13]

Participants

6

Reactant 4

HCID 24437Sodium SulfiteHCID 70297m-Chloroperbenzoic acid2×HCID 516892Sodium Bicarbonate2×HCID 86639422HCID 86639422, compound

Product 1

HCID 86639421HCID 86639421, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-[2-Propyl-4-(2,2,2-trifluoro-1-methoxymethoxy-1-trifluoromethyl-ethyl)-phen oxy]-2-vinyl-benzonitrile (14 mg, 0.030 mmol) was dissolved in dichloromethane (300 μL). The resultant mixture was added with sodium hydrogen carbonate (7.5 mg, 0.089 mmol) and 3-chloroperoxybenzoic acid (8.5 mg, 0.030 mmol) under ice-cold conditions and stirred at room temperature for 1.5 hours. Subsequently, the resultant mixture was further added with sodium hydrogen carbonate (7.5 mg, 0.089 mmol) and 3-chloroperoxybenzoic acid (8.5 mg, 0.030 mmol) under ice-cold conditions and stirred at room temperature overnight. The reaction solution was added with a saturated aqueous solution of sodium sulfite and a saturated aqueous solution of sodium hydrogen carbonate, and extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium hydrogen carbonate and brine, dried over sodium sulfate, and concentrated in vacuo. The obtained residue was purified using silica-gel column chromatography (hexane/ethyl acetate), and 2-oxiranyl-5-[2-propyl-4-(2,2,2-trifluoro-1-methoxymethoxy-1-trifluoromethyl-ethyl)-phenoxy]-benzonitrile (5.5 mg, yield 38%) was obtained as a yellow oil.

Workup

  1. stirringstirred at room temperature overnight
  2. extractiona saturated aqueous solution of sodium hydrogen carbonate, and extracted with ethyl acetate
  3. washThe organic layer was washed with a saturated aqueous solution of sodium hydrogen carbonate and brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe obtained residue was purified

Sources & evidence

ORD record
ord-c37fd5b8fdc8404fa29fcff3310556c1
Source dataset
uspto-grants-2012_04
Patent number
US08153634B2

Reaction notes

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