Lithium Hydroxide → HCID 69830469, compound

HRID 1017593Notes

Reaction equation

HRID 1017593 reaction equation
C[O:2][C:3](=[O:21])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH2:12][C@@H:13]2[CH2:17][O:16][C:15]([CH3:19])([CH3:18])[O:14]2)[C:6]=1[CH3:20].[OH-].[Li+]>CO>[CH3:18][C:15]1([CH3:19])[O:14][C@H:13]([CH2:12][O:11][C:7]2[C:6]([CH3:20])=[C:5]([CH2:4][C:3]([OH:21])=[O:2])[CH:10]=[CH:9][CH:8]=2)[CH2:17][O:16]1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 69831028HCID 69831028, compound

Product 1

HCID 69830469HCID 69830469, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-diazo-1-[3-(2,2-dimethyl-[1,3]-dioxolan-4-ylmethoxy)-2-methylphenyl]ethanone (0.5 g, 1.73 mmol) in 20 mL of methanol at room temperature was added dropwise a solution of silver benzoate (52 mg, 13%) in 2.6 mL of triethylamine. The solution turned greenish and then brown, black precipitate formed. After stirring for 1.5 h, it was filtered through celite and the filtrate was concentrated. The residue was then purified on a silica gel column with 20% ethyl acetate in hexane to afford 0.43 g of [3-((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-2-methylphenyl] acetic acid methyl ester. The above ester was then hydrolyzed by stirring with lithium hydroxide (0.25 g) in 5 mL of methanol at room temperature to give 0.4 g of [3-((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-2-methylphenyl] acetic acid.

Sources & evidence

ORD record
ord-3b80364d463d42b19e258503cb457717
Source dataset
uspto-grants-2002_11
Patent number
US06479490B2

Reaction notes

Loading…