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

HRID 1461414ノート

反応式

HRID 1461414 の反応式
[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

参加物

5

反応物 2

HCID 80803,4-dihydro-2H-pyranHCID 130526324-((2-Hydroxyethyl)thio)phenol2 回

生成物 1

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

試薬・触媒・溶媒 2

HCID 6101p-Toluenesulfonic acid触媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

17.91 g of 2-hydroxyethyl 4-hydroxyphenyl sulfide prepared by the above process (1) was dissolved in 280 m(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:

後処理

  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

出典と根拠

ORDレコード
ord-44721a6d72594be4bdd63e2662ef2c47
出典データセット
uspto-grants-1991_12
特許番号
US05075335

反応ノート

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