Lithium Hydroxide → HCID 69830566, compound

HRID 1017596Notes

Reaction equation

HRID 1017596 reaction equation
C[O:2][C:3](=[O:23])[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[N+:20]([O-:22])=[O:21].[OH-].[Li+]>CO>[CH3:18][C:15]1([CH3:19])[O:14][C@H:13]([CH2:12][O:11][C:7]2[C:6]([N+:20]([O-:22])=[O:21])=[C:5]([CH2:4][C:3]([OH:23])=[O:2])[CH:10]=[CH:9][CH:8]=2)[CH2:17][O:16]1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 69831344HCID 69831344, compound

Product 1

HCID 69830566HCID 69830566, compoundYield 100.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-diazo-1-[3-(2,2-dimethyl-[1,3]-dioxolan-4-ylmethoxy)-2-nitrophenyl]ethanone (0.9 g, 2.8 mmol) in 30 mL of methanol at room temperature was added dropwise a solution of silver benzoate (84 mg, 13%) in 4.2 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 0.75 g of [3-((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-2-nitrophenyl] acetic acid methyl ester. The above ester (0.52 g, 1.6 mmol) was then hydrolyzed by stirring with lithium hydroxide (0.27 g) in 5 mL of methanol at room temperature to give 0.5 g of [3-((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-2-nitrophenyl] acetic acid.

Sources & evidence

ORD record
ord-ef343b1e5bd84ea085bbf3597801762e
Source dataset
uspto-grants-2002_11
Patent number
US06479490B2

Reaction notes

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