Benzyl Alcohol → Benzyl 4-mercaptobutyrate

HRID 2296679ノート

反応式

HRID 2296679 の反応式
[H-].[Na+].[CH2:3]([OH:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:11]1(=[S:16])[O:15][CH2:14][CH2:13][CH2:12]1.O>O1CCCC1>[SH:16][CH2:11][CH2:12][CH2:13][C:14]([O:10][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[O:15]

参加物

6

反応物 4

HCID 244Benzyl AlcoholHCID 962WaterHCID 24758Sodium hydrideHCID 11073360THIOBUTYROLACTONE

生成物 1

HCID 18387499Benzyl 4-mercaptobutyrate収率 102.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

反応条件

温度
0 °C

実験手順

Sodium hydride (60% in oil dispersion, 1.22 g, 50.9 mmol) was washed with dry tetrahydrofuran (20 ml×3) under nitrogen atomosphere. Freshly distilled tetrahydrofuran (50 ml) was added and the mixture was cooled to 0° C. with an ice bath. To this mixture was added portionwise solution of benzyl alcohol (5 g, 46.2 mmol) in dry tetrahydrofuran (10 ml) and the mixture was stirred for 1 hour at said temperature. To the resulting mixture was added γ-thiobutyrolactone (5.2 g, 50.9 mmol) slowly and the resulting mixture was warmed to room temperature. After stirring for 1 hour, H2O(30 ml) was added carefully and tetrahydrofuran was removed under reduced pressure. The residue was extracted three times with AcOEt. The organic layers were combined, washed with brine, and dried over magnesium sulfate. The solvent was evaporated to give 9.96 g of benzyl 4mercaptobutyrate as a colorless oil which was taken to the next step without further purification.

後処理

  1. temperaturethe resulting mixture was warmed to room temperature
  2. stirringAfter stirring for 1 hour
  3. customtetrahydrofuran was removed under reduced pressure
  4. extractionThe residue was extracted three times with AcOEt
  5. washwashed with brine
  6. dry with materialdried over magnesium sulfate
  7. customThe solvent was evaporated

出典と根拠

ORDレコード
ord-0cea55de276f42c9a2805382b7f6bc05
出典データセット
uspto-grants-2002_12
特許番号
US06489324B2

反応ノート

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