Diethyl Ether → 1-Dimethylsulfamoyl-2-t-butyldimethylsilyl-5-imidazolecarboxaldehyde

HRID 2269189Notes

Reaction equation

[Li]CCCC.[CH3:6][N:7]([CH3:30])[S:8]([N:11]1[C:15](SC2C=CC=CC=2)=[CH:14][N:13]=[C:12]1[Si:23]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24])(=[O:10])=[O:9].[CH2:31]([O:33]CC)C>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:30][N:7]([CH3:6])[S:8]([N:11]1[C:15]([CH:31]=[O:33])=[CH:14][N:13]=[C:12]1[Si:23]([C:26]([CH3:28])([CH3:29])[CH3:27])([CH3:24])[CH3:25])(=[O:10])=[O:9]

Participants

Conditions

Temperature: -70 °C

Procedure

Methyl triphenylphosphonium bromide (2.75 g, 7.70 mmol) was suspended in 50 mL of diethyl ether. At −10° C., nBuLi (3.08 mL, 7.70 mmol, 2.5M soln in hexanes) was added. This mixture was stirred for 35 m before cooling to −70° C. A solution of (R)-(+)-4,4a,5,6,7,8-hexahydro-4a-methyl-2(3H)-naphthalenone (1) (1.0 g, 6.09 mmol) in 15 mL of ether was added via syringe. This mixture was warmed to 0° C. over 30 m and the stirred at rt for another 30 m. The solution was washed with brine (2×20 mL) dried over MgSO4, filtered and the solvent was removed. Chromatography on SiO2 with hexanes gave 0.82 g (83%) of the diene 2 as a clear colorless oil.

Workup

temperatureThis mixture was warmed to 0° C. over 30 m
stirringthe stirred at rt for another 30 m
washThe solution was washed with brine (2×20 mL)
dry with materialdried over MgSO4
filtrationfiltered
customthe solvent was removed

Sources & evidence

ORD record: ord-0563553934564d918acd74105721efeb
Source dataset: uspto-grants-2001_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06329369B1

Reaction notes

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