Benzyl Alcohol → Benzyl 4-mercaptobutyrate

HRID 2271031노트

반응식

HRID 2271031 반응식
[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]

참가 물질

6

반응물 4

HCID 244Benzyl AlcoholHCID 962WaterHCID 24758Sodium hydrideHCID 11073360THIOBUTYROLACTONE

생성물 1

HCID 18387499Benzyl 4-mercaptobutyrate수율 102.5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

반응 조건

온도
0 °C

실험 절차

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 4-mercaptobutyrate as a colorless oil which was taken to the next step without further purification.

후처리

  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

출처 및 근거

ORD 기록
ord-ec780771bf154a0f84ac4709a5e2086b
출처 데이터셋
uspto-grants-2001_12
특허 번호
US06333324B1

반응 노트

불러오는 중…