5-((Tert-butyldimethylsilyl)oxy)pentan-1-ol → 3-[6-(tert-Butyldimethylsilyloxy)-1-[(4-chlorophenyl)sulfonyl]hexyl]-2-chloropyridine

HRID 748719Notes

Reaction equation

HRID 748719 reaction equation
[Cl:1][C:2]1[C:7]([CH2:8][S:9]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)(=[O:11])=[O:10])=[CH:6][CH:5]=[CH:4][N:3]=1.[Si:19]([O:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]O)([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20].C(C=P(CCCC)(CCCC)CCCC)#N>C1(C)C=CC=CC=1>[Si:19]([O:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH:8]([C:7]1[C:2]([Cl:1])=[N:3][CH:4]=[CH:5][CH:6]=1)[S:9]([C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=1)(=[O:11])=[O:10])([C:22]([CH3:23])([CH3:24])[CH3:25])([CH3:20])[CH3:21]

Participants

5

Reactant 3

HCID 36143185-((Tert-butyldimethylsilyl)oxy)pentan-1-olHCID 4622928CyanomethylenetributylphosphoraneHCID 230286692-Chloro-3-(4-chlorophenylsulfonylmethyl)pyridine

Product 1

HCID 597508833-[6-(tert-Butyldimethylsilyloxy)-1-[(4-chlorophenyl)sulfonyl]hexyl]-2-chloropyridine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A toluene (5 ml) solution of the 2-chloro-3-(4-chlorophenylsulfonylmethyl)pyridine (200 mg, 0.662 mmol) obtained in Example 98, 5-(tert-butyldimethylsilyloxy)pentanol (288 mg, 1.32 mmol) and cyanomethylenetri-n-butylphosphorane (318 mg, 1.32 mmol) was heated under reflux for 22 hours under an argon atmosphere. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure. The residue was subjected to flash chromatography on a silica gel column, and the fraction obtained from the 15% ethyl acetate/hexane eluate was concentrated under reduced pressure, whereby the title compound (307 mg, 92%) was obtained as a colorless oil.

Workup

  1. temperatureunder reflux for 22 hours under an argon atmosphere
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. customthe fraction obtained from the 15% ethyl acetate/hexane eluate
  4. concentrationwas concentrated under reduced pressure, whereby the title compound (307 mg, 92%)
  5. customwas obtained as a colorless oil

Sources & evidence

ORD record
ord-2dc6d845b92849e6b7f98b0734a08233
Source dataset
uspto-grants-2008_07
Patent number
US07399775B2

Reaction notes

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