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

HRID 1760477노트

반응식

HRID 1760477 반응식
[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]

참가 물질

5

반응물 3

HCID 9357Potassium Sodium TartrateHCID 14487Diisobutylaluminum hydrideHCID 53770328HCID 53770328, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

반응 조건

온도
-78 °C

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-d8809bba5a7c4bdba470b6756cac79a7
출처 데이터셋
uspto-grants-2005_01
특허 번호
US06841684B2

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