Oleyl p-toluenesulfonate → HCID 70256374, 화합물

HRID 376416

반응식

HRID 376416 반응식
[O:1]1[CH2:5][CH2:4][CH2:3][CH:2]1[O:6][CH:7]([CH2:10][OH:11])[CH2:8][OH:9].[C:12](O[K])([CH3:15])([CH3:14])C.C1(C)C=CC(S(O[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35]/[CH:36]=[CH:37]\[CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH3:45])(=O)=O)=CC=1>C1(C)C(C)=CC=CC=1>[CH2:45]([O:11][CH2:10][CH:7]([CH2:8][O:9][CH2:42][CH2:41][CH2:40][CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]/[CH:34]=[CH:33]\[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:14][CH2:12][CH3:15])[O:6][CH:2]1[CH2:3][CH2:4][CH2:5][O:1]1)[CH2:44][CH2:43][CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]/[CH:37]=[CH:36]\[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH3:28]

참가 물질

5

반응물 3

HCID 11258749Oleyl p-toluenesulfonateHCID 19361256HCID 19361256, 화합물HCID 178418922HCID 178418922, 화합물

생성물 1

HCID 70256374HCID 70256374, 화합물수율 18%

시약·촉매·용매 1

HCID 7237O-Xylene용매2회

실험 절차

In 30 ml of xylene was dissolved 854 mg (5.3 mmol) of 2-O-tetrahydrofuranylglycerol. To this was added 1.78 g (15.9 mmol) of t-butoxypotassium under argon gas and the mixture was stirred for 5 minutes. Then, 10 ml of a solution of 6.71 g (15.9 mmol) oleyl p-toluenesulfonate in xylene was added dropwise and the mixture was stirred under reduced pressure (20-30 mmHg) at ambient temperature for 30 minutes and further at 50° C. for 1 hour. This reaction mixture was poured in ice-water and extracted with ether, and the extract was washed with water, dried, and concentrated. The residue was purified by column chromatography (silica gel/chloroform) to provide 628 mg (18%) of 1,3-O-dioleyl-2-O-tetrahydrofuranylglycerol as yellow oil. (5) In 30 ml of tetrahydrofuran was dissolved 628 mg (0.95 mmol) of 1,3-O-dioleyl-2-O-tetrahydrofuranylglycerol followed by addition of 5 ml of diluted (10%) hydrochloric acid, and the mixture was stirred overnight. The reaction mixture was then diluted with water, neutralized with saturated aqueous sodium hydrogen carbonate solution, and extracted with ether. The extract was dried and concentrated and the residue was subjected to column chromatography (silica gel/n-hexane-ethyl acetate) to provide 321 mg (57%) of the title compound as colorless oil.

후처리

  1. stirringthe mixture was stirred under reduced pressure (20-30 mmHg) at ambient temperature for 30 minutes and further at 50° C. for 1 hour
  2. extractionextracted with ether
  3. washthe extract was washed with water
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography (silica gel/chloroform)

출처 및 근거

ORD 기록
ord-462aa6735f5049069925dc7e93bf77c6
출처 데이터셋
uspto-grants-2000_02
특허 번호
US06020317

연결된 노트

불러오는 중…