Sodium Thiosulfate → HCID 59201126, compound

HRID 1690155Notes

Reaction equation

HRID 1690155 reaction equation
[F:1][C:2]([F:31])([F:30])[C:3]([C:12]1[CH:17]=[CH:16][C:15]([O:18][C:19]2[CH:24]=[CH:23][C:22]([CH:25]=[CH2:26])=[CH:21][CH:20]=2)=[C:14]([CH2:27][CH2:28][CH3:29])[CH:13]=1)([O:8][CH2:9][O:10][CH3:11])[C:4]([F:7])([F:6])[F:5].C(=O)([O-])[OH:33].[Na+].ClC1C=CC=C(C(OO)=O)C=1.S([O-])([O-])(=O)=S.[Na+].[Na+].C([BH3-])#N.[Na+]>C(Cl)(Cl)Cl.O1CCCC1>[F:1][C:2]([F:30])([F:31])[C:3]([C:12]1[CH:17]=[CH:16][C:15]([O:18][C:19]2[CH:20]=[CH:21][C:22]([CH2:25][CH2:26][OH:33])=[CH:23][CH:24]=2)=[C:14]([CH2:27][CH2:28][CH3:29])[CH:13]=1)([O:8][CH2:9][O:10][CH3:11])[C:4]([F:6])([F:5])[F:7]

Participants

8

Reactant 5

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium Bicarbonate2×HCID 5003444Sodium cyanoborohydrideHCID 59200942HCID 59200942, compound

Product 1

HCID 59201126HCID 59201126, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(1,1,1,3,3,3-hexafluoro-2-(methoxymethoxy)propan-2-yl)-2-propyl-1-(4-vinylphenoxy)benzene (242 mg, 539 mmol) in chloroform (5 mL), sodium hydrogen carbonate (181 mg) and m-chloroperbenzoic acid (60%) (310 mg) were added at room temperature and the resultant mixture was stirred. After completion of the reaction, the reaction solution was added with an aqueous solution of sodium thiosulfate and a saturated aqueous solution of sodium hydrogen carbonate, extracted with ethyl acetate, and then concentrated in vacuo. The obtained residue was purified using silica-gel column chromatography (hexane/ethyl acetate) and a colorless oil was obtained. To a tetrahydrofuran solution (2 mL) of this substance, boron trifluoride diethyl ether complex (40 μL) and sodium cyanoborohydride (40 mg) were added at 0° C. under an argon atmosphere, and the resultant mixture was stirred. After completion of the reaction, the reaction solution was added with a saturated aqueous solution of sodium hydrogen carbonate, extracted with ethyl acetate, and then concentrated in vacuo. The obtained residue was purified using silica-gel column chromatography (hexane/ethyl acetate) and the title compound (76 mg, yield 30%) was obtained as a colorless oil.

Workup

  1. customAfter completion of the reaction
  2. extractiona saturated aqueous solution of sodium hydrogen carbonate, extracted with ethyl acetate
  3. concentrationconcentrated in vacuo
  4. customThe obtained residue was purified
  5. customa colorless oil was obtained
  6. customAfter completion of the reaction
  7. extractionextracted with ethyl acetate
  8. concentrationconcentrated in vacuo
  9. customThe obtained residue was purified

Sources & evidence

ORD record
ord-74d6ba5776214ff280cb94a7f1660a5b
Source dataset
uspto-grants-2012_04
Patent number
US08153634B2

Reaction notes

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