3,4-dihydro-2H-pyran → 4-Hydroxyphenyl 2-(tetrahydropyran-2-yloxy)ethyl sulfide

HRID 2292128노트

반응식

HRID 2292128 반응식
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:9][CH2:10][OH:11])=[CH:4][CH:3]=1.[O:12]1[CH:17]=[CH:16][CH2:15][CH2:14][CH2:13]1>O1CCCC1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[O:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH:13]1[O:11][CH2:10][CH2:9][S:8][C:5]1[CH:4]=[CH:3][C:2]([OH:1])=[CH:7][CH:6]=1

참가 물질

5

반응물 2

HCID 80803,4-dihydro-2H-pyranHCID 130526324-((2-Hydroxyethyl)thio)phenol2회

생성물 1

HCID 140519404-Hydroxyphenyl 2-(tetrahydropyran-2-yloxy)ethyl sulfide수율 58%

시약·촉매·용매 2

HCID 6101p-Toluenesulfonic acid촉매HCID 8028Tetrahydrofuran용매2회

실험 절차

17.91 g of 2-hydroxyethyl 4-hydroxyphenyl sulfide prepared by the above process (1) was dissolved in 280 ml of tetrahydrofuran. 0.18 g of p-toluenesulfonic acid was added to the solution. A solution of 17.69 g of 3,4-dihydro-2H-pyran in 140 ml of tetrahydrofuran was added dropwise to the mixture under cooling with ice and then the mixture was stirred at room temperature for 4 h. The solvent was distilled off and the residue was extracted with diethyl ether, washed with an aqueous sodium hydrocarbonate solution and dried over anhydrous magnesium sulfate. The resulting solution was filtered and the filtrate was concentrated and subjected to silica gel column chromatography to obtain 15.38 g (yield: 58%) of the intended compound having the following physical properties:

후처리

  1. temperatureunder cooling with ice
  2. distillationThe solvent was distilled off
  3. extractionthe residue was extracted with diethyl ether
  4. washwashed with an aqueous sodium hydrocarbonate solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationThe resulting solution was filtered
  7. concentrationthe filtrate was concentrated

출처 및 근거

ORD 기록
ord-6d7cbf8c41ce41a89266b2263655f0c8
출처 데이터셋
uspto-grants-1989_01
특허 번호
US04801603

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