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

HRID 748719노트

반응식

HRID 748719 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-2dc6d845b92849e6b7f98b0734a08233
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07399775B2

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