Water → HCID 59590853, compound

HRID 2098963Notes

Reaction equation

C[Si]([N-][Si](C)(C)C)(C)C.[Li+].C[Si](C)(C)[CH2:13][C:14]([O:16][CH3:17])=[O:15].[N+:20]([C:23]1[CH:32]=[C:31]2[C:26]([CH2:27][CH2:28][CH2:29][C:30]2=O)=[CH:25][CH:24]=1)([O-:22])=[O:21].O>C1COCC1>[N+:20]([C:23]1[CH:32]=[C:31]2[C:26]([CH2:27][CH2:28][CH2:29]/[C:30]/2=[CH:13]\[C:14]([O:16][CH3:17])=[O:15])=[CH:25][CH:24]=1)([O-:22])=[O:21]

Participants

Conditions

Temperature: -78 °C

Procedure

At −78° C., lithium bis(trimethylsilyl)amide, (1.0 M in hexanes) (5 mL, 28 mmol) was added slowly to a solution of methyl 2-(trimethylsilyl)acetate (4 g, 28 mmol) in THF (30 mL). The reaction was maintained at −78° C. for 16 minutes and then 7-nitro-1-tetralone 6.1 (available from Astratech) (3 g, 16 mmol) was added in one portion, and the resulting mixture was stirred at −78° C. and allowed to warm to room temperature for 20 hours. The resulting mixture was poured into water (30 mL) and then extracted with EtOAc (300 mL). The combined organic layers were washed with brine and dried over anhydrous sodium sulfate. After removing solvent, the residue was purified by chromatography (silica gel, 1:4 EtOAc/hexane) to give 6.2 in 83% yield.

Workup

temperatureto warm to room temperature for 20 hours
extractionextracted with EtOAc (300 mL)
washThe combined organic layers were washed with brine
dry with materialdried over anhydrous sodium sulfate
customAfter removing solvent
customthe residue was purified by chromatography (silica gel, 1:4 EtOAc/hexane)
customto give 6.2 in 83% yield

Sources & evidence

ORD record: ord-4d3ec2a32f5048f2bf46c6d28dee7767
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08450522B2

Reaction notes

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