Cyanomethylenetributylphosphorane → HCID 59750788, compound

HRID 748757Notes

Reaction equation

HRID 748757 reaction equation
[CH2:1]([N:8]1[N:12]=[N:11][C:10]([CH:13]([S:20]([C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=2)(=[O:22])=[O:21])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]O)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(C=P(CCCC)(CCCC)CCCC)#N>C1(C)C=CC=CC=1>[CH2:1]([N:8]1[N:12]=[N:11][C:10]([C:13]2([S:20]([C:23]3[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=3)(=[O:22])=[O:21])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 4622928CyanomethylenetributylphosphoraneHCID 59750818HCID 59750818, compound

Product 1

HCID 59750788HCID 59750788, compoundYield 57.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a toluene (3 ml) solution of 6-(2-benzyl-2H-tetrazol-5-yl)-6-[(4-chlorophenyl)sulfonyl]-1-hexanol (145 mg, 0.33 mmol) was added a toluene (3 ml) solution of cyanomethylenetri-n-butylphosphorane (179 mg, 0.67 m=ol). The resulting mixture was heated under reflux for 7 hours. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure. The residue was subjected to flash silica gel chromatography and the fraction obtained from the hexane:ethyl acetate=4:1 eluate was concentrated under reduced pressure. The resulting solid was washed with hexane/diethyl ether and collected by filtration, whereby the title compound (78 mg, 0.19 mmol, 56%) was obtained as a white solid.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureunder reflux for 7 hours
  3. concentrationthe reaction mixture was concentrated under reduced pressure
  4. customthe fraction obtained from the hexane
  5. concentrationethyl acetate=4:1 eluate was concentrated under reduced pressure
  6. washThe resulting solid was washed with hexane/diethyl ether

Sources & evidence

ORD record
ord-d5b4e71cf0db49e8af6e6bf0222eaabb
Source dataset
uspto-grants-2008_07
Patent number
US07399775B2

Reaction notes

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