Toluene → 2-(3-Oxetanyl)butyltosylate

HRID 732843

反応式

HRID 732843 の反応式
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[C:12]1([CH3:18])[CH:17]=[CH:16]C=[CH:14][CH:13]=1.C(C1C[O:23][CH:22]1CO)C.[OH-:27].[Na+]>[Br-].C[N+](C)(C)C.O>[O:23]1[CH2:16][CH:17]([CH:12]([CH2:13][CH3:14])[CH2:18][O:8][S:7]([C:4]2[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=2)(=[O:27])=[O:9])[CH2:22]1

参加物

7

反応物 4

HCID 1140TolueneHCID 73974-Toluenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 219084763-Ethyl-hydroxymethyloxetane

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

To a 2000-ml three-necked flask including a thermometer, a condenser, a stirrer and a dropping funnel were added 190.65 g (1.0 mol) of p-toluenesulfonic acid chloride, 32.24 g (0.1 mol) of tetramethylammonium bromide and 400 ml of toluene, which in turn were cooled down to 5° C. while being stirred in an ice bath. After 116.16 g (1.0 mmol) of 3-ethyl-hydroxymethyl-oxetane was added to the mixture, 130 ml of 35% by weight of a sodium hydroxide aqueous solution was dropped from the dropping funnel over 30 minutes. After the completion of the dropping, the above-mentioned flask was stirred at the same temperature for one hour, and was further stirred at room temperature (25° C.) for 16 hours. After the completion of a reaction, 800 ml of water was added into the above-mentioned flask, and was stirred violently. Thereafter, the resultant mixture was allowed to stand until the mixture separated into an aqueous phase and an organic phase. The organic phase was further cleaned with 400 ml of water, and was dried overnight with anhydrous magnesium sulfate. Thereafter, magnesium sulfate was filtered off, and the filtrate was concentrated. A crude product thus obtained was separated and purified by silica gel column chromatography (an eluate: hexane/ethyl acetate) to synthesize 243.3 g (in a yield of 90%) of 2-(3-oxetanyl)butyltosylate which was an intended colorless liquid.

後処理

  1. customTo a 2000-ml three-necked flask including
  2. additionwas dropped from the dropping funnel over 30 minutes
  3. stirringAfter the completion of the dropping, the above-mentioned flask was stirred at the same temperature for one hour
  4. stirringwas further stirred at room temperature (25° C.) for 16 hours
  5. additionwas added into the above-mentioned flask
  6. stirringwas stirred violently
  7. customseparated into an aqueous phase
  8. dry with materialwas dried overnight with anhydrous magnesium sulfate
  9. filtrationThereafter, magnesium sulfate was filtered off
  10. concentrationthe filtrate was concentrated

出典と根拠

ORDレコード
ord-56591d8975684e9d8c8ed5603de891ee
出典データセット
uspto-grants-2009_09
特許番号
US07587113B2

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