Water → 2,3-Dihydrobenzo(b)thiophene

HRID 546255

反応式

HRID 546255 の反応式
[S:1]1(=O)(=O)[CH2:5][CH2:4][C:3]2[CH:6]=[CH:7][CH:8]=[CH:9][C:2]1=2.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>C(OCC)C.Cl>[S:1]1[CH2:5][CH2:4][C:3]2[CH:6]=[CH:7][CH:8]=[CH:9][C:2]1=2

参加物

6

反応物 3

HCID 962WaterHCID 2844232,3-Dihydro-1lambda6-benzothiophene-1,1-dioneHCID 21226445Aluminium lithium hydride

生成物 1

HCID 783192,3-Dihydrobenzo(b)thiophene収率 46%

試薬・触媒・溶媒 2

HCID 313Hydrochloric Acid溶媒HCID 3283Diethyl Ether溶媒2 回

反応条件

温度
0 °C

実験手順

A suspension of 2,3-dihydro-benzo[b]thiophene 1,1-dioxide (5.06 g, 30.08 mmol) in diethyl ether (150 mL) was added to a suspension of lithium aluminum hydride (10.27 g, 270.27 mmol) in diethyl ether (150 mL) at 25° C. After this time it was heated to reflux for 4 h (caution: if heating is too rapid it can exotherm rapidly and cause loss of material through the reflux condenser). It was then cooled to 0° C. in an ice bath and water (50 mL) was added very slowly. The resulting material was dissolved in 4 M aqueous hydrochloric acid (1 L). The aqueous layer was then extracted with diethyl ether (3×200 mL). The organic layers were combined and dried over magnesium sulfate, filtered and concentrated in vacuo. The material was purified by passing it through a plug of silica gel using pentane as the solvent to afford 2,3-dihydro-benzo[b]thiophene (1.88 g, 46%) as a clear colorless oil.

後処理

  1. temperatureAfter this time it was heated
  2. temperatureto reflux for 4 h (caution
  3. temperatureif heating
  4. extractionThe aqueous layer was then extracted with diethyl ether (3×200 mL)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe material was purified

出典と根拠

ORDレコード
ord-11fb6e12e91a4bf2bad0804052390e4c
出典データセット
uspto-grants-2011_05
特許番号
US07935699B2

関連ノート

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