Ammonium Chloride → HCID 18442173, compound

HRID 458485Notes

Reaction equation

HRID 458485 reaction equation
Cl[CH2:2][Si:3]([CH3:6])([CH3:5])[CH3:4].[Mg].[C:8]([O:13][C:14]1([CH2:21][CH3:22])[CH2:18][CH2:17][CH2:16][CH:15]1CC)(=[O:12])[C:9]([O-])=[O:10].[Cl-].[NH4+]>C(OCC)C>[OH:10][C:9]([CH2:2][Si:3]([CH3:6])([CH3:5])[CH3:4])([CH2:2][Si:3]([CH3:6])([CH3:5])[CH3:4])[C:8]([O:13][C:14]1([CH2:21][CH3:22])[CH2:18][CH2:17][CH2:16][CH2:15]1)=[O:12]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 75361Silane, (chloromethyl)trimethyl-HCID 5462224MagnesiumHCID 86591716HCID 86591716, compound

Product 1

HCID 18442173HCID 18442173, compoundYield 78.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Under a nitrogen atmosphere, a Grignard reagent solution was prepared from 100 g of chloromethyltrimethylsilane, 20 g of magnesium and 500 ml of diethyl ether. Under a nitrogen atmosphere, the Grignard reagent solution was slowly added dropwise to a solution of 80 g of ethyl(1-ethylcyclopentyl) oxalate (which had been prepared by reacting ethyl chloroglyoxylate and 1-ethylcyclopentanol in pyridine) in 360 ml of diethyl ether at −40° C. After 2 hours of stirring at the temperature, the solution was warmed up to room temperature and stirred for further 8 hours. An aqueous solution of ammonium chloride was added for hydrolysis, followed by usual work-up procedure including extraction, washing, drying and concentration to give 102 g (crude yield 79%) of crude 1-ethylcyclopentyl 2-hydroxy-3-trimethylsilyl-2-trimethylsilylmethylpropionate.

Workup

  1. stirringstirred for further 8 hours
  2. extractionextraction
  3. washwashing
  4. customdrying
  5. concentrationconcentration

Sources & evidence

ORD record
ord-06b8ac20010a4ed4a695494244b9584b
Source dataset
uspto-grants-2007_03
Patent number
US07192684B2

Reaction notes

Loading…