Potassium Sodium Tartrate → 5-(2,3-Dihydrobenzo[1,4]dioxin-6-ylmethyl)-4-methylimidazole-1-sulfonic acid dimethylamide

HRID 1760477ノート

反応式

HRID 1760477 の反応式
[CH3:1][N:2]([CH3:31])[S:3]([N:6]1[C:10]([CH:11]([C:13]2[CH:22]=[CH:21][C:16]3[O:17][CH2:18][CH2:19][O:20][C:15]=3[CH:14]=2)O)=[C:9]([CH3:23])[N:8]=[C:7]1[Si](C(C)(C)C)(C)C)(=[O:5])=[O:4].CC(C[AlH]CC(C)C)C.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>C(OCC)C>[CH3:31][N:2]([CH3:1])[S:3]([N:6]1[C:10]([CH2:11][C:13]2[CH:22]=[CH:21][C:16]3[O:17][CH2:18][CH2:19][O:20][C:15]=3[CH:14]=2)=[C:9]([CH3:23])[N:8]=[CH:7]1)(=[O:4])=[O:5]

参加物

5

反応物 3

HCID 9357Potassium Sodium TartrateHCID 14487Diisobutylaluminum hydrideHCID 53770328HCID 53770328、化合物

生成物 1

HCID 207117805-(2,3-Dihydrobenzo[1,4]dioxin-6-ylmethyl)-4-methylimidazole-1-sulfonic acid dimethylamide

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

反応条件

温度
-78 °C

実験手順

A solution of the above ethyl ester 3 (1.0 g, 5.9 mmol) was dissolved in hexanes (50 mL) and cooled to −78° C. A solution of DIBAL (5.8 mL 1.0 M in cyclohexane) was added dropwise. After 15 m, diethyl ether (50 mL) was added and the mixture was stirred with Rochelle's salt solution (25 mL) for 10 m. The organic layer was separated, dried and filtered. Chromatography on SiO2 with 7% Et2O:Hx delivered the aldehyde as a clear colorless oil, 0.52 g (74%). The aldehyde 4 was subjected to the Büchi protocol as described above. The fumarate salt of the imidazole 5 (U-1) was obtained in three steps (25% overall).

後処理

  1. customThe organic layer was separated
  2. customdried
  3. filtrationfiltered

出典と根拠

ORDレコード
ord-d8809bba5a7c4bdba470b6756cac79a7
出典データセット
uspto-grants-2005_01
特許番号
US06841684B2

反応ノート

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