4-Toluenesulfonyl chloride → [3-(2-Hydroxybut-3-yn-2-yl)isoxazol-5-yl]methyl 4-methylbenzenesulfonate

HRID 1398541노트

반응식

HRID 1398541 반응식
[OH:1][CH2:2][C:3]1[O:7][N:6]=[C:5]([C:8]([OH:12])([C:10]#[CH:11])[CH3:9])[CH:4]=1.C(N(CC)CC)C.[C:20]1([CH3:30])[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=1>C(Cl)Cl>[CH3:30][C:20]1[CH:25]=[CH:24][C:23]([S:26]([O:1][CH2:2][C:3]2[O:7][N:6]=[C:5]([C:8]([OH:12])([C:10]#[CH:11])[CH3:9])[CH:4]=2)(=[O:28])=[O:27])=[CH:22][CH:21]=1

참가 물질

5

반응물 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 866695832-[5-(Hydroxymethyl)isoxazol-3-yl]but-3-yn-2-ol

생성물 1

HCID 86669584[3-(2-Hydroxybut-3-yn-2-yl)isoxazol-5-yl]methyl 4-methylbenzenesulfonate

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a solution of 2-[5-(hydroxymethyl)isoxazol-3-yl]but-3-yn-2-ol (500 mg, 2.99 mmol) in DCM (5 mL) at 0° C. under an atmosphere of nitrogen was introduced triethylamine (333 mg, 3.29 mmol) and p-toluenesulfonyl chloride (627 mg, 3.29 mmol) in one portion. After warming to RT for 3 hr, the reaction mixture was diluted with DCM (10 mL) and washed with brine (5 mL). The organic extract was dried (Na2SO4), filtered and the filtrate adsorbed onto silica gel in vacuo. Purification by silica gel flash column chromatography (heptane/EtOAc gradient of increasing polarity) furnished the title compound as a colorless oil: 1H NMR (500 MHz, CDCl3) delta 1.84 (3H, s), 2.26 (3H, s), 2.66 (1H, s), 2.86 (1H, br. s), 5.14 (2H, s), 6.41 (1H, s), 7.36 (2H, d, J=8.1 Hz), 7.80 (2H, d, J=8.1 Hz); LC-MS: m/z=+321.9 (M+H)+.

후처리

  1. washwashed with brine (5 mL)
  2. extractionThe organic extract
  3. dry with materialwas dried (Na2SO4)
  4. filtrationfiltered
  5. customPurification
  6. temperatureby silica gel flash column chromatography (heptane/EtOAc gradient of increasing polarity)

출처 및 근거

ORD 기록
ord-9659975df37248a9a1c4f5da4880c309
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08901313B2

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