Methyl chloroglyoxylate → HCID 22166479, compound

HRID 2298505Notes

Reaction equation

HRID 2298505 reaction equation
Br[CH2:2][CH2:3][C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5].Cl[C:12](=[O:17])[C:13]([O:15][CH3:16])=[O:14].C(OC(CCCCCC(=O)C(OC)=O)=O)(C)(C)C>[Zn]>[C:7]([O:6][C:4]([CH2:3][CH2:2][C:12](=[O:17])[C:13]([O:15][CH3:16])=[O:14])=[O:5])([CH3:10])([CH3:9])[CH3:8]

Participants

5

Reactant 3

HCID 79846Methyl chloroglyoxylateHCID 256128tert-Butyl 3-bromopropionateHCID 18338592HCID 18338592, compound

Product 1

HCID 22166479HCID 22166479, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 23994ZincCatalyst

Procedure

3-Bromopropanoic acid, tert-butyl ester (2.2 g, 10.6 mmol), activated zinc (1.25 g in 25 ml of THF) and methyl chlorooxoacetate (1.4 ml, 11.4 mmol) were reacted by the same procedure as described in Example 1 for the preparation of methyl 7-tert-butyoxycarbonyl-2-oxoheptanoate to give the crude title material (1.65 g) as a colorless liquid which is used directly in next step.

Sources & evidence

ORD record
ord-a980c43a838b419d8fe3bccf20912274
Source dataset
uspto-grants-2002_12
Patent number
US06492550B2

Reaction notes

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