4-Toluenesulfonyl chloride → Iodopropargyl 4methylbenzenesulfonate

HRID 258241ノート

反応式

HRID 258241 の反応式
[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

参加物

6

反応物 3

HCID 73974-Toluenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 602749Iodopropargyl alcohol

生成物 1

HCID 18321752Iodopropargyl 4methylbenzenesulfonate収率 93.4%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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 4-methylbenzenesulfonate as an off-white solid, mp=75°-78° C. An NMR spectrum showed the desired compound.

後処理

  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

出典と根拠

ORDレコード
ord-46753b27d9034d9db66249b95f4476f7
出典データセット
uspto-grants-1993_11
特許番号
US05266567

反応ノート

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