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4-Toluenesulfonyl chloride → (4R)-4-p-toluenesulfonyloxy-2-[4-(4-methoxyphenyl)phenyl]decanenitrile

HRID 973518
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HRID 973518 반응식
[OH:1][C@H:2]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH2:3][CH:4]([C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)=[CH:9][CH:8]=1)[C:5]#[N:6].[C:27]1([CH3:37])[CH:32]=[CH:31][C:30]([S:33](Cl)(=[O:35])=[O:34])=[CH:29][CH:28]=1>N1C=CC=CC=1.CN(C1C=CN=CC=1)C>[C:27]1([CH3:37])[CH:32]=[CH:31][C:30]([S:33]([O:1][C@H:2]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH2:3][CH:4]([C:7]2[CH:12]=[CH:11][C:10]([C:13]3[CH:14]=[CH:15][C:16]([O:19][CH3:20])=[CH:17][CH:18]=3)=[CH:9][CH:8]=2)[C:5]#[N:6])(=[O:35])=[O:34])=[CH:29][CH:28]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 2

HCID 73974-Toluenesulfonyl chlorideHCID 54327812(4R)-4-hydroxy-2-[4-(4-methoxyphenyl)phenyl]decanenitrile

생성물 1

HCID 54083752(4R)-4-p-toluenesulfonyloxy-2-[4-(4-methoxyphenyl)phenyl]decanenitrile수율 49%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 1049Pyridine용매2회

실험 절차

To a solution of 186 mg (0.53 mmol) of (4R)-4-hydroxy-2-[4-(4-methoxyphenyl)phenyl]decanenitrile in 10 ml of pyridine were added a solution of 303 mg (1.6 mmol) of p-toluenesulfonyl chloride in 20 ml of pyridine and 10 mg of DMAP. The resulting mixture was stirred at room temperature overnight. The pyridine was then removed by evaporation under reduced pressure. The residue was separated and purified by column chromatography (hexane/ethyl acetate=4/1), thereby obtaining 130 mg (yield 49%) of (4R)-4-p-toluenesulfonyloxy-2-[4-(4-methoxyphenyl)phenyl]decanenitrile.

후처리

  1. customThe pyridine was then removed by evaporation under reduced pressure
  2. customThe residue was separated
  3. custompurified by column chromatography (hexane/ethyl acetate=4/1)

출처 및 근거

ORD 기록
ord-caaa7fb22bcb4b298337ad3f9e892a95
출처 데이터셋
uspto-grants-1991_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05064564

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