Toluene → 2-(3-Oxetanyl)butyltosylate

HRID 15254

反応式

HRID 15254 の反応式
[Cl-].[C:2]1([CH3:12])[CH:7]=[CH:6][C:5]([S:8]([O-:11])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[C:13]1([CH3:19])[CH:18]=[CH:17]C=[CH:15][CH:14]=1.C(C1C[O:24][CH:23]1CO)C.[OH-].[Na+]>[Br-].C[N+](C)(C)C.O>[O:24]1[CH2:17][CH:18]([CH:13]([CH2:14][CH3:15])[CH2:19][O:10][S:8]([C:5]2[CH:4]=[CH:3][C:2]([CH3:12])=[CH:7][CH:6]=2)(=[O:11])=[O:9])[CH2:23]1

参加物

7

反応物 4

HCID 1140TolueneHCID 14798Sodium HydroxideHCID 219084763-Ethyl-hydroxymethyloxetaneHCID 22024621HCID 22024621、化合物

生成物 1

HCID 866155722-(3-Oxetanyl)butyltosylate収率 90%

試薬・触媒・溶媒 2

HCID 66137Tetramethylammonium bromide触媒HCID 962Water溶媒

反応条件

温度
5 °C

実験手順

Into a 2000 ml three-neck flask having a thermometer, a cooler, a stirring device, and a dripping funnel, 190.65 g (1.0 mol) of p-toluene sulfonate chloride, 32.24 g (0.1 mol) of tetramethylammonium bromide, and 400 ml of toluene were poured and cooled to 5° C. with stirring in an ice bath. After pouring 116.16 g (1.0 mmol) of 3-ethyl-hydroxymethyloxetane into the three-neck flask, 130 ml of a 35 wt % sodium hydroxide solution was dripped into the three-neck flask in 30 minutes. After the dripping, stirring was continued for 1 hour at the same temperature and then for 16 hours at a room temperature. After the reaction, 800 ml of water was poured into the flask followed by violent stirring. The mixture was left to stand to separate a water phase from an organic phase. The organic phase was washed with 400 ml of water and then dried with anhydrous magnesium sulfate over night. Then, the magnesium sulfate was removed by filtration, and the filtrate was concentrated. The thus-obtained crude product was separated and purified by silica gel column chromatography (eluting solution: hexane/ethyl acetate) to obtain a desired substance, i.e. 243.3 g (yield: 90%) of 2-(3-oxetanyl)butyltosylate as a colorless liquid.

後処理

  1. customInto a 2000 ml three-neck flask having
  2. stirringAfter the dripping, stirring
  3. waitwas continued for 1 hour at the same temperature
  4. waitfor 16 hours at a room temperature
  5. additionwas poured into the flask
  6. waitThe mixture was left
  7. customto separate a water phase from an organic phase
  8. washThe organic phase was washed with 400 ml of water
  9. dry with materialdried with anhydrous magnesium sulfate over night
  10. customThen, the magnesium sulfate was removed by filtration
  11. concentrationthe filtrate was concentrated
  12. customThe thus-obtained crude product
  13. customwas separated
  14. custompurified by silica gel column chromatography (eluting solution: hexane/ethyl acetate)

出典と根拠

ORDレコード
ord-b949bd80aeba4604a5a286cd02a5fb03
出典データセット
uspto-grants-2010_06
特許番号
US07732562B2

関連ノート

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