Methyl acetoacetate → 5-Hydroxy-6-methyl-5-[2-(4-methyl-thiazol-5-yl)ethyl]-3-oxo-heptanoic acid methyl ester

HRID 23451Notes

Reaction equation

[C:1]([O:7][CH3:8])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[H-].[Na+].[Li]CCCC.[CH3:16][CH:17]([CH3:28])[C:18](=[O:27])[CH2:19][CH2:20][C:21]1[S:25][CH:24]=[N:23][C:22]=1[CH3:26]>>[CH3:8][O:7][C:1](=[O:6])[CH2:2][C:3](=[O:4])[CH2:5][C:18]([OH:27])([CH2:19][CH2:20][C:21]1[S:25][CH:24]=[N:23][C:22]=1[CH3:26])[CH:17]([CH3:16])[CH3:28]

Participants

Reactant 4

HCID 7757Methyl acetoacetate

HCID 24758Sodium hydride

HCID 225727814-Methyl-1-(4-methyl-thiazol-5-yl)-pentan-3-one

HCID 178418339Butyllithium

Product 1

HCID 539015915-Hydroxy-6-methyl-5-[2-(4-methyl-thiazol-5-yl)ethyl]-3-oxo-heptanoic acid methyl ester

Procedure

The title compound was prepared as described in General Method 6 from 1.00 g (8.61 mmol) of methyl acetoacetate, 0.38 g (9.50 mmol) of sodium hydride, 4.5 mL of 2.1 M nBuLi (9.45 mmol), and 1.53 g (7.75 mmol) of 4-methyl-1-(4-methyl-thiazol-5-yl)-pentan-3-one (prepared in Example C-2.) The crude compound was used without purification in the next step.

Workup

customwas used without purification in the next step

Sources & evidence

ORD record: ord-303f294555e14ece87a8f0eeaa350c19
Source dataset: uspto-grants-2005_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06852711B2

Reaction notes

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