Hexane → HCID 59750891, compound

HRID 748768Notes

Reaction equation

HRID 748768 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH2:11][C:12]2[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=2[F:19])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[S:20]1[CH:24]=[CH:23][CH:22]=[C:21]1[CH2:25][CH2:26]O.C(C=P(CCCC)(CCCC)CCCC)#N.CCCCCC>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH:11]([C:12]2[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=2[F:19])[CH2:26][CH2:25][C:21]2[S:20][CH:24]=[CH:23][CH:22]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8058HexaneHCID 794002-ThiopheneethanolHCID 4622928CyanomethylenetributylphosphoraneHCID 99010282-(((4-Chlorophenyl)sulfonyl)methyl)-1,4-difluorobenzene

Product 1

HCID 59750891HCID 59750891, compoundYield 66.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Under an argon atmosphere, the 2-[(4-chlorophenyl)sulfonylmethyl]-1,4-difluorobenzene (100 mg, 0.330 mmol) obtained in Example 5 and 2-(2-thienyl)ethanol (144 mg, 1.32 mmol) were dissolved in toluene (3 ml), followed by the addition of cyanomethylenetri-n-butylphosphorane (159 mg, 0.660 mmol). The resulting mixture was heated under reflux for 15 hours under a nitrogen atmosphere. The reaction mixture was then concentrated. The residue thus obtained was subjected to flash chromatography on a silica gel column, and the fraction obtained from the hexane:ethyl acetate=12:1 eluate was concentrated, whereby the title compound (90.0 mg, 0.218 mmol, 53%) was obtained as a colorless oil.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureunder reflux for 15 hours under a nitrogen atmosphere
  3. concentrationThe reaction mixture was then concentrated
  4. customThe residue thus obtained
  5. concentrationethyl acetate=12:1 eluate was concentrated

Sources & evidence

ORD record
ord-df2e57d8210a493db0a38ad85fe8e506
Source dataset
uspto-grants-2008_07
Patent number
US07399775B2

Reaction notes

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