Ethylene Glycol → 2-(3-{2-[2-(2-{2-Azidoethoxy}ethoxy)ethoxy]ethoxy}-4,5-dimethoxyphenyl)-1,3-dioxolane

HRID 1510973ノート

反応式

HRID 1510973 の反応式
[N:1]([CH2:4][CH2:5][O:6][CH2:7][CH2:8][O:9][CH2:10][CH2:11][O:12][CH2:13][CH2:14][O:15][C:16]1[CH:17]=[C:18]([CH:21]=[C:22]([O:26][CH3:27])[C:23]=1[O:24][CH3:25])[CH:19]=[O:20])=[N+:2]=[N-:3].[CH2:28](O)[CH2:29][OH:30].C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[N:1]([CH2:4][CH2:5][O:6][CH2:7][CH2:8][O:9][CH2:10][CH2:11][O:12][CH2:13][CH2:14][O:15][C:16]1[CH:17]=[C:18]([CH:19]2[O:30][CH2:29][CH2:28][O:20]2)[CH:21]=[C:22]([O:26][CH3:27])[C:23]=1[O:24][CH3:25])=[N+:2]=[N-:3]

参加物

6

反応物 3

HCID 174Ethylene GlycolHCID 516892Sodium BicarbonateHCID 866321223-{2-[2-(2-{2-Azidoethoxy}ethoxy)ethoxy]ethoxy}-4,5-dimethoxybenzaldehyde

生成物 1

HCID 866321212-(3-{2-[2-(2-{2-Azidoethoxy}ethoxy)ethoxy]ethoxy}-4,5-dimethoxyphenyl)-1,3-dioxolane収率 83.7%

試薬・触媒・溶媒 2

HCID 521998p-Toluenesulfonic acid monohydrate触媒HCID 1140Toluene溶媒

実験手順

A mixture of 4.95 g (12.91 mmol) 3-{2-[2-(2-{2-azidoethoxy}ethoxy)ethoxy]ethoxy}-4,5-dimethoxybenzaidehyde 8, 5 ml (5.57 g, 90 mmol) ethylene glycol and 200 mg (1.0 mmol) p-toluene sulfonic acid monohydrate was refluxed in 120 ml of toluene for 8 hrs using a Dean-Stark trap. After cooling to room temperature the rection mixture was poured into 200 ml of diluted sodium bicarbonate solution, washed with water and brine and dried over magnesium sulfate. After removal of the solvent the residue was purified by silica gel column chromatography (cyclohexane/ethyl acetate 1/1), giving 4.43 g (10.8 mmol, 80%) of the product as a clear oil. 1H-NMR (CDCl3) δ=6.73 (dd, 2H, J=5.0 Hz, J=1.8 Hz), 5.72 (s, 1H), 4.19 (m, 2H), 4.11 (m, 2H), 4.03 (m, 2H), 3.87 (s, 3H), 3.84 (s, 3H), 3.76-3.71 (m, 4H), 3.70-3.64 (m, 8H), 3.37 (m, 2H) ppm. 13C-NMR δ=153.3, 152.4, 139.2, 133.1, 105.4, 103.6, 103.4, 70.7, 70.6, 70.5 (2 peaks), 69.9, 69.6, 68.7, 65.1, 60.6, 56.0, 50.6 ppm. MS: m/z=427 [M]+. Anal. calcd for C19H29N3O8: C, 53.39, H, 6.84, N, 9.83. Found C, 52.30, H, 6.89, N, 9.72.

後処理

  1. washwashed with water and brine
  2. dry with materialdried over magnesium sulfate
  3. customAfter removal of the solvent the residue
  4. customwas purified by silica gel column chromatography (cyclohexane/ethyl acetate 1/1)

出典と根拠

ORDレコード
ord-fe28c53da1ca4ecca6145d7e78291f8e
出典データセット
uspto-grants-2012_07
特許番号
US08212058B2

反応ノート

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