4-Toluenesulfonyl chloride → Iodopropargyl 4methylbenzenesulfonate

HRID 1707732노트

반응식

HRID 1707732 반응식
[I:1][CH:2]([OH:5])[C:3]#[CH:4].[OH-].[Na+].[C:8]1([CH3:18])[CH:13]=[CH:12][C:11]([S:14](Cl)(=[O:16])=[O:15])=[CH:10][CH:9]=1>C1COCC1.O>[CH3:18][C:8]1[CH:13]=[CH:12][C:11]([S:14]([O:5][CH:2]([I:1])[C:3]#[CH:4])(=[O:16])=[O:15])=[CH:10][CH:9]=1

참가 물질

6

반응물 3

HCID 73974-Toluenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 602749Iodopropargyl alcohol

생성물 1

HCID 18321752Iodopropargyl 4methylbenzenesulfonate수율 93.4%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회

실험 절차

Into a 500 mL 4-neck round bottom flask, equipped with a magnetic stirrer and an addition funnel, in an ice bath were placed iodopropargyl alcohol (10 g, 54.9 mmol) in THF (20 mL) and sodium hydroxide (3.4 g, 84.6 mmol) in water (20 mL) To the above cold mixture was added a solution of p-toluenesulfonyl chloride (10.4 g, 54.95 mmol) in THF (20 mL) from an addition funnel. The reaction mixture was stirred for 2 hrs. below 5° C. The reaction mixture was then poured into ice water and the precipitate was collected by suction-filtration and washed with water. After drying under vacuum, the precipitate afforded 17.2 g (yield: 93.4%) of iodopropargyl 4methylbenzenesulfonate as an off-white solid, mp=75°-78 ° C. An NMR spectrum showed the desired compound.

후처리

  1. customInto a 500 mL 4-neck round bottom flask, equipped with a magnetic stirrer and an addition funnel, in an ice bath
  2. custombelow 5° C
  3. filtrationthe precipitate was collected by suction-filtration
  4. washwashed with water
  5. customAfter drying under vacuum

출처 및 근거

ORD 기록
ord-f4540bce37fd44068fb0339b5d7f80b7
출처 데이터셋
uspto-grants-1994_10
특허 번호
US05354862

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