Diethylene Glycol → Tetrahydropyranyldiethyleneglycol

HRID 2276825ノート

反応式

HRID 2276825 の反応式
[CH2:1]([OH:7])[CH2:2][O:3][CH2:4][CH2:5][OH:6].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[O:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1>C(Cl)Cl>[O:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH:21]1[O:7][CH2:1][CH2:2][O:3][CH2:4][CH2:5][OH:6]

参加物

5

反応物 3

HCID 8117Diethylene GlycolHCID 8894TetrahydropyranHCID 521998p-Toluenesulfonic acid monohydrate

生成物 1

HCID 558984Tetrahydropyranyldiethyleneglycol収率 57%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To 800 mL of CH2Cl2 were added diethylene glycol (57 mL, 0.6 mol) and p-toluenesulfonic acid monohydrate (5.7 g, 30 mmol) successively. Then tetrahydropyran (27.4 mL, 0.3 mol) was added dropwise at 0° C. The reaction mixture was stirred overnight and quenched with H2O, extracted with CH2Cl2, washed with H2O and brine successively, concentrated through rotary evaporation, and subjected to silica gel chromatography using CH2Cl2/MeOH as the eluent to afford compound 28 (32.5 g, 0.17 mol, 57% yield) as a clear oil: 1H NMR (500 MHz, CDCl3) δ 4.59 (t, J=4.0 Hz, 1H), 3.85-3.80 (m, 2H), 3.68-3.64 (m, 4H), 3.59-3.55 (m, 3H), 3.48-3.44 (m, 1H), 2.98 (br, 1H), 1.81-1.76 (m, 1H), 1.71-1.65 (m, 1H), 1.59-1.46 (m, 4H).

後処理

  1. customquenched with H2O
  2. extractionextracted with CH2Cl2
  3. washwashed with H2O and brine successively
  4. concentrationconcentrated through rotary evaporation

出典と根拠

ORDレコード
ord-7222c64e82ab460cade0a3f4f65a016c
出典データセット
uspto-grants-2015_09
特許番号
US09133114B2

反応ノート

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