Water → HCID 86709902, compound

HRID 341341Notes

Reaction equation

HRID 341341 reaction equation
[C:1]([C:3]([CH2:15][Si:16]1([CH3:21])[CH2:20][CH2:19][CH2:18][CH2:17]1)([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])C(OCC)=O)#[N:2].O.[Br-].[Li+]>CN(C)C=O>[CH3:21][Si:16]1([CH2:15][CH:3]([C:1]#[N:2])[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

5

Reactant 3

HCID 962WaterHCID 82050Lithium BromideHCID 86709903HCID 86709903, compound

Product 1

HCID 86709902HCID 86709902, compoundYield 88.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Diethyl 2-cyano-2-[(1-methyl-1-silacyclopentan-1-yl)methyl]succinate (1.943 g, 6.25 mmol) was treated with water and lithium bromide in dimethylformamide in the same manner as that of Example 15. The reaction mixture was treated in a conventional manner, and the residue was purified by silica gel column chromatography [hexane/ethyl acetate (14:1)] to obtain ethyl 4-(1-methyl-1-silacyclopentan-1-yl)-3-cyanobutanoate (1.321 g, 88%) mentioned in the title was obtained as colorless oil.

Workup

  1. additionThe reaction mixture was treated in a conventional manner
  2. customthe residue was purified by silica gel column chromatography [hexane/ethyl acetate (14:1)]

Sources & evidence

ORD record
ord-f0d290055d2944b59c7dd3bc3b171a72
Source dataset
uspto-grants-2014_11
Patent number
US08895769B2

Reaction notes

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