Ethylene Glycol → 5,5-(Ethylenedioxy)-4a-methyl-2,3,4,4a,5,6,7,8-octahydronaphtalen-2-one

HRID 551297ノート

反応式

HRID 551297 の反応式
[CH3:1][C:2]12[C:12](=[O:13])[CH2:11][CH2:10][CH2:9][C:8]1=[CH:7][C:5](=[O:6])[CH2:4][CH2:3]2.[CH3:14][C:15]1(CC)OCC[O:16]1.C(O)CO>O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH2:14]1[CH2:15][O:16][C:12]2([CH2:11][CH2:10][CH2:9][C:8]3[C:2]2([CH3:1])[CH2:3][CH2:4][C:5](=[O:6])[CH:7]=3)[O:13]1

参加物

5

反応物 3

HCID 174Ethylene GlycolHCID 610672-Ethyl-2-methyl-1,3-dioxolaneHCID 89262(+-)-Wieland-Miescher ketone

生成物 1

HCID 109221015,5-(Ethylenedioxy)-4a-methyl-2,3,4,4a,5,6,7,8-octahydronaphtalen-2-one収率 94%

試薬・触媒・溶媒 1

HCID 521998p-Toluenesulfonic acid monohydrate触媒

実験手順

A mixture of Wieland-Miescher ketone (5.086 g, 28.44 mmol), 2-methyl-2-ethyl-1,3-dioxolane (19.38 mL, 155.0 mmol), ethylene glycol (0.358 mL, 6.43 mmol) and p-toluenesulfonic acid monohydrate (0.4 g, 2.13 mmol) was stirred at room temperature for 30 hours. The reaction was quenched with dropwise addition of triethylamine, diluted with 20 mL of benzene, washed with water, dried over MgSO4, and concentrated under vacuum. The product was triturated from hexanes to yield monoacetal 201 (5.92 g, 94%). 1H NMR (CDCl3) δ 1.36 (s, 3H), 1.6-2.0 (m, 5H), 2.2-2.5 (m, 5H), 3.9-4.1 (m, 4H), 5.80 (d, J=Hz, 1H); 13C NMR (CDCl3) 198.91, 167.55, 125.38, 125.37, 112.12, 65.16, 64.84, 44.81, 33.70, 31.22, 29.81, 26.62, 21.51, 20.27.

後処理

  1. customThe reaction was quenched with dropwise addition of triethylamine
  2. additiondiluted with 20 mL of benzene
  3. washwashed with water
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under vacuum
  6. customThe product was triturated from hexanes

出典と根拠

ORDレコード
ord-b7ec16b91fc34df79b8ff3a4403399d6
出典データセット
uspto-grants-2011_05
特許番号
US07947726B2

反応ノート

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