Methyl chloroglyoxylate → HCID 18338591, compound

HRID 2298502Notes

Reaction equation

HRID 2298502 reaction equation
Br[CH2:2][CH2:3][CH2:4][C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6].Cl[C:13](=[O:18])[C:14]([O:16][CH3:17])=[O:15].C(OC(CCCCCC(=O)C(OC)=O)=O)(C)(C)C>[Zn]>[C:8]([O:7][C:5]([CH2:4][CH2:3][CH2:2][C:13](=[O:18])[C:14]([O:16][CH3:17])=[O:15])=[O:6])([CH3:11])([CH3:10])[CH3:9]

Participants

5

Reactant 3

HCID 79846Methyl chloroglyoxylateHCID 2757253tert-Butyl 4-bromobutanoateHCID 18338592HCID 18338592, compound

Product 1

HCID 18338591HCID 18338591, compoundYield 85.4%

Reagents, catalysts & solvents 1

HCID 23994ZincCatalyst

Procedure

t-Butyl 4-bromobutanoate (1.22 g, 5.49 mmol), activated zinc (0.75 g in 15 ml of THF) and methyl chlorooxoacetate (0.74 ml, 6 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 (1.08 g) as a colorless liquid which is used directly in next step.

Sources & evidence

ORD record
ord-83b06f4820144f77b0f436f7d079b5c5
Source dataset
uspto-grants-2002_12
Patent number
US06492550B2

Reaction notes

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