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

HRID 1760477Notes

Reaction equation

[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]

Participants

Conditions

Temperature: -78 °C

Procedure

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).

Workup

customThe organic layer was separated
customdried
filtrationfiltered

Sources & evidence

ORD record: ord-d8809bba5a7c4bdba470b6756cac79a7
Source dataset: uspto-grants-2005_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06841684B2

Reaction notes

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