Hydrochloric Acid → HCID 70673735, compound

HRID 341339Notes

Reaction equation

HRID 341339 reaction equation
[CH3:1][Si:2]1([CH:8]=[CH:9][C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:11])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.C1CCN2C(=NCCC2)CC1.Cl.[N+:32]([CH3:35])([O-:34])=[O:33]>>[N+:32]([CH2:35][CH:8]([Si:2]1([CH3:1])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1)[CH2:9][C:10]([O:12][CH2:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)=[O:11])([O-:34])=[O:33]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 6375NitromethaneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 86709900HCID 86709900, compound

Product 1

HCID 70673735HCID 70673735, compoundYield 72%

Procedure

A solution of benzyl 3-(1-methyl-1-silacyclohexan-1-yl)acrylate (1.940 g, 7.08 mmol) in nitromethane (5 ml) was cooled on ice, and added with DBU (0.26 ml, 1.74 mmol), and the mixture was stirred for 30 minutes, and further stirred at room temperature for 17 hours. The reaction mixture was added with aqueous hydrochloric acid (1 N), the mixture was extracted with ethyl acetate, and the organic layer was washed with saturated aqueous sodium hydrogencarbonate, and then treated in a conventional manner. The residue was purified by silica gel column chromatography [hexane/ethyl acetate (14:1)] to obtain benzyl 4-nitro-3-(1-methyl-1-silacyclohexan-1-yl)butanoate (1.711 g, 72%) mentioned in the title as colorless oil.

Workup

  1. stirringfurther stirred at room temperature for 17 hours
  2. extractionthe mixture was extracted with ethyl acetate
  3. washthe organic layer was washed with saturated aqueous sodium hydrogencarbonate
  4. additiontreated in a conventional manner
  5. customThe residue was purified by silica gel column chromatography [hexane/ethyl acetate (14:1)]

Sources & evidence

ORD record
ord-ad82f44129e6474192b410b1cd4d4bdc
Source dataset
uspto-grants-2014_11
Patent number
US08895769B2

Reaction notes

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