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

HRID 2269191Notes

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-23b2bdf891aa4c44ae5afd6de7829cc5
Source dataset: uspto-grants-2001_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06329369B1

Reaction notes

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