Diethyl Oxalate → HCID 13411633, compound

HRID 458484Notes

Reaction equation

HRID 458484 reaction equation
[C:1]([O:8][CH2:9][CH3:10])(=[O:7])[C:2](OCC)=[O:3].Cl[CH2:12][Si:13]([CH3:16])([CH3:15])[CH3:14].[Mg].[Cl-].[NH4+]>O1CCCC1>[OH:3][C:2]([CH2:12][Si:13]([CH3:16])([CH3:15])[CH3:14])([CH2:12][Si:13]([CH3:16])([CH3:15])[CH3:14])[C:1]([O:8][CH2:9][CH3:10])=[O:7]

Participants

6

Reactant 4

HCID 7268Diethyl OxalateHCID 25517Ammonium ChlorideHCID 75361Silane, (chloromethyl)trimethyl-HCID 5462224Magnesium

Product 1

HCID 13411633HCID 13411633, compoundYield 94.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Under a nitrogen atmosphere and with ice cooling, a solution of 293 g diethyl oxalate in 500 ml tetrahydrofuran was slowly added dropwise to a Grignard reagent solution which had been prepared from 540 g of chloromethyltrimethylsilane, 107 g of magnesium and 2,000 ml of tetrahydrofuran. The solution was stirred for 3 hours at room temperature, after which an aqueous solution of ammonium chloride was added for hydrolysis. Usual work-up procedure including extraction, washing, drying and concentration yielded 525 g (crude yield 95%) of ethyl 2-hydroxy-3-trimethylsilyl-2-trimethylsilylmethylpropionate.

Workup

  1. extractionextraction
  2. washwashing
  3. customdrying
  4. concentrationconcentration

Sources & evidence

ORD record
ord-58cf3e944a874f10b659b9509956ef8d
Source dataset
uspto-grants-2007_03
Patent number
US07192684B2

Reaction notes

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