4-Toluenesulfonyl chloride → pent-4-ynyl tosylate

HRID 606049노트

반응식

HRID 606049 반응식
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[CH2:12]([OH:17])[CH2:13][CH2:14][C:15]#[CH:16].C(N(CC)CC)C>ClCCl>[CH3:11][C:1]1[CH:6]=[CH:5][C:4]([S:7]([O:17][CH2:12][CH2:13][CH2:14][C:15]#[CH:16])(=[O:9])=[O:8])=[CH:3][CH:2]=1

참가 물질

5

반응물 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 793464-Pentyn-1-ol

생성물 1

HCID 10966564pent-4-ynyl tosylate수율 87%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

p-Toluenesulfonyl chloride (21.4 g, 112 mmol) was added slowly to a stirred solution of 4-pentyn-1-ol (11.5 mL, 124 mL) and triethylamine (17.2 mL, 124 mmol) in dichloromethane (100 mL) at room temperature. After 22 hours, the solution was diluted with dichloromethane, washed with water, dried over sodium sulfate, filtered, and concentrated. The crude product was purified by flash chromatography (silica gel, gradient elution from 95:5 to 85:15 hexanes/ethyl acetate) to afford the product pent-4-ynyl 4-methylbenzenesulfonate (23.4 g, 87%) as a colorless oil.

후처리

  1. washwashed with water
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product was purified by flash chromatography (silica gel, gradient elution from 95:5 to 85:15 hexanes/ethyl acetate)

출처 및 근거

ORD 기록
ord-cb613e99fa82443e9122e343e7d282e5
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07915281B2

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