Dimethylamine → 2-(Dimethylamino)ethyl 5-(tetradecyloxy)furan-2-carboxylate

HRID 335537

反応式

HRID 335537 の反応式
[CH2:1]([O:15][C:16]1[O:20][C:19]([C:21]([O:23][CH2:24][CH2:25]Br)=[O:22])=[CH:18][CH:17]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].[CH3:27][NH:28][CH3:29]>C1COCC1>[CH2:1]([O:15][C:16]1[O:20][C:19]([C:21]([O:23][CH2:24][CH2:25][N:28]([CH3:29])[CH3:27])=[O:22])=[CH:18][CH:17]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

参加物

4

反応物 2

HCID 674DimethylamineHCID 498698992-Bromoethyl 5-(tetradecyloxy)furan-2-carboxylate

生成物 1

HCID 498701652-(Dimethylamino)ethyl 5-(tetradecyloxy)furan-2-carboxylate収率 71%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a solution of 2-bromoethyl 5-(tetradecyloxy)furan-2-carboxylate (0.186 g, 0.43 mmol) (prepared in Example 5) in THF at 0° C. was added dimethylamine (1 mL of a 2M solution in THF, 2.15 mmol) with stirring. The solution was allowed to warm to room temperature and stirring was continued for 12 hrs at which time the reaction was concentrated to dryness. The crude material was purified by flash chromatography eluting with ethyl acetate in hexanes (5-35%) to yield 0.121 g (71%) of the title compound as a waxy, colourless solid. MS (m/z, ES+): 396.29 (M+1, 100%); 1H NMR (400 MHz, DMSO-d6) δ: 7.2 (d, 1H), 5.6 (d, 1H), 4.23 (t, 2H), 4.13 (t, 2H), 2.53 (t, 2H), 2.18 (s, 6H), 1.7 (p, 2H), 1.2-1.5 (m, 22H), 0.85 (t, 3H).

後処理

  1. stirringstirring
  2. concentrationthe reaction was concentrated to dryness
  3. customThe crude material was purified by flash chromatography
  4. washeluting with ethyl acetate in hexanes (5-35%)

出典と根拠

ORDレコード
ord-887bb610d8174f36a0850033d1a95458
出典データセット
uspto-grants-2014_11
特許番号
US08884034B2

関連ノート

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