Water → HCID 21332560, compound

HRID 1390527Notes

Reaction equation

HRID 1390527 reaction equation
[N:1]([O-:3])=[O:2].[Na+].Br[CH2:6][CH2:7][CH2:8][CH2:9][Si:10]([CH3:13])([CH3:12])[CH3:11].O>CS(C)=O>[N+:1]([CH2:6][CH2:7][CH2:8][CH2:9][Si:10]([CH3:13])([CH3:12])[CH3:11])([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 962WaterHCID 12845802HCID 12845802, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 21332560HCID 21332560, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

4-Nitrobutyltrimethylsilane was prepared as follows: To a solution of 1.9 g (0.028 mol) of sodium nitrite in 30 ml of dimethyl sulfoxide was added 2.92 g (0.014 mol) of 4-bromobutyltrimethylsilane. After 3 hrs, 30 ml of water was added and the mixture was extracted with three 15 ml portions of carbon tetrachloride. The carbon tetrachloride solution was washed with 10 ml of water and dried over magnesium sulfate. The NMR spectrum showed 30% nitrite ester (CH2ONOδ4.57), and 70% nitro compound. Distillation gave 1.1 g (45%) of 4-nitrobutyltrimethylsilane, bp 54°-6° (0.9 mm).

Workup

  1. custom4-Nitrobutyltrimethylsilane was prepared
  2. extractionthe mixture was extracted with three 15 ml portions of carbon tetrachloride
  3. washThe carbon tetrachloride solution was washed with 10 ml of water
  4. dry with materialdried over magnesium sulfate
  5. distillationDistillation

Sources & evidence

ORD record
ord-cf178d94a196491cb4162cc4d2da41ee
Source dataset
uspto-grants-1979_02
Patent number
US04139403

Reaction notes

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