p-Toluenesulfonic acid → 1-Benzyloxy-4-(2-tetrahydropyran-2-yloxyethyl)benzene

HRID 34406

反応式

HRID 34406 の反応式
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][OH:17])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[O:29]1[CH:34]=[CH:33][CH2:32][CH2:31][CH2:30]1>C(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][CH2:16][O:17][CH:30]2[CH2:31][CH2:32][CH2:33][CH2:34][O:29]2)=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 6101p-Toluenesulfonic acidHCID 80803,4-dihydro-2H-pyranHCID 3017260p-(Benzyloxy)phenethyl alcohol

生成物 1

HCID 142087821-Benzyloxy-4-(2-tetrahydropyran-2-yloxyethyl)benzene

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 1-benzyloxy-4-(2-hydroxyethyl)benzene (7, 20 g, 87.7 mmoles) in CH2Cl2 (175 mL) was added 4-toluenesulfonic acid (TsOH, 0.17 g, 0.9 mmoles) and dihydropyran (9.9 mL dropwise, 108 mmoles). The mixture was stirred for 4 h and the solvent evaporated under reduced pressure to yield 28 g of crude product. This was purified by flash chromatography (solvent=70:30 ethyl acetate:heptane). The pure fractions were pooled and the solvent evaporated to give 1-benzyloxy-4-(2-tetrahydropyran-2-yloxyethyl)benzene (8, 26.5 g). NMR (CDCl3)δppm: 7.30(s, 5H); 6.97(q, 4H); 4.95(s, 2H); 7.87(s, 1H); 4.2-3.4(m, 4H); 2.8(t, 2H); 1.9-1.3(m, 6H). (Scheme II, Step 3.)

後処理

  1. customthe solvent evaporated under reduced pressure
  2. customto yield 28 g of crude product
  3. customThis was purified by flash chromatography (solvent=70:30 ethyl acetate:heptane)
  4. customthe solvent evaporated

出典と根拠

ORDレコード
ord-f92efd1f6d3f4d53b725d2188aaf8482
出典データセット
uspto-grants-1988_08
特許番号
US04761420

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