Hexane → HCID 59750825, compound

HRID 748795Notes

Reaction equation

HRID 748795 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]2([C:17]3[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:18]=3[F:24])[CH2:16][CH2:15][S:14][CH2:13][CH2:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.ClC1C=CC=C(C(OO)=[O:33])C=1.CCCCCC>ClCCl.C(OCC)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]2([C:17]3[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:18]=3[F:24])[CH2:16][CH2:15][S:14](=[O:33])[CH2:13][CH2:12]2)(=[O:9])=[O:10])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 8058HexaneHCID 70297m-Chloroperbenzoic acidHCID 59750738HCID 59750738, compound

Product 1

HCID 59750825HCID 59750825, compoundYield 79.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

In dichloromethane (30 ml) was dissolved 4-[(4-chlorophenyl)sulfonyl]-4-(2,5-difluorophenyl)tetrahydrothiopyran (200 mg, 0.508 mmol). Under ice cooling, 3-chloroperbenzoic acid (106 mg, 0.614 mmol) was added. After stirring at room temperature for 14 hours, the reaction mixture was concentrated under reduced pressure. The residue thus obtained was subjected to flash silica gel chromatography, and the fraction obtained from the hexane:ethyl acetate=1:1 eluate was concentrated under reduced pressure to give a white solid. The white solid was washed with diethyl ether, whereby the title compound (163 mg, 0.403 mmol, 79%) was obtained as a white powder.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. customThe residue thus obtained
  3. concentrationethyl acetate=1:1 eluate was concentrated under reduced pressure
  4. customto give a white solid

Sources & evidence

ORD record
ord-a34daab4055448c49cc22432ea4e03a3
Source dataset
uspto-grants-2008_07
Patent number
US07399775B2

Reaction notes

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