Methanol → 4-Hydroxy-cyclopent-2-ene-1,2-dicarboxylic acid 2-methyl ester

HRID 1429191Notes

Reaction equation

HRID 1429191 reaction equation
[Li+].[OH-].[CH3:3][O:4][C:5]([CH:7]1[CH2:11][CH:10]([OH:12])[CH:9]=[C:8]1[C:13]([O:15]C)=[O:14])=[O:6].C1(C)C=CC=CC=1.CO>O1CCOCC1.O>[CH3:3][O:4][C:5]([C:7]1[CH:8]([C:13]([OH:15])=[O:14])[CH2:9][CH:10]([OH:12])[CH:11]=1)=[O:6]

Participants

7

Reactant 4

HCID 887MethanolHCID 1140TolueneHCID 3939Lithium HydroxideHCID 591654434-Hydroxy-cyclopent-2-ene-1,2-dicarboxylic acid dimethyl ester

Product 1

HCID 591654534-Hydroxy-cyclopent-2-ene-1,2-dicarboxylic acid 2-methyl esterYield 27%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

LiOH (0.52 g, 22 mmol) was added to an ice-cold solution of the alcohol 23b (3.4 g, 22 mmol) dissolved in dioxane and water (1:1, 110 mL). After two and a half hours the mixture was co-evaporated with toluene and methanol. Purification by flash chromatography (toluene/Ethyl acetate 3:1+1% HOAc) gave the title compound (1.0 g, 27%) as yellow-white crystals.

Workup

  1. customPurification by flash chromatography (toluene/Ethyl acetate 3:1+1% HOAc)

Sources & evidence

ORD record
ord-56c4bad20964462d9e7c683aa98dea7e
Source dataset
uspto-grants-2015_01
Patent number
US08937080B2

Reaction notes

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