Methanol → (E)-3-(4-pyrrolidin-1-ylmethylphenyl)acrylic Acid

HRID 735165Notes

Reaction equation

HRID 735165 reaction equation
[N:1]1([CH2:6][C:7]2[CH:12]=[CH:11][C:10](/[CH:13]=[CH:14]/[C:15]([O:17]CC)=[O:16])=[CH:9][CH:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.O.[OH-].[Li+].CO.C1COCC1>O>[N:1]1([CH2:6][C:7]2[CH:12]=[CH:11][C:10](/[CH:13]=[CH:14]/[C:15]([OH:17])=[O:16])=[CH:9][CH:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 68817431ethyl(E)-3-(4-pyrrolidin-1-ylmethylphenyl)acrylate

Product 1

HCID 68815843(E)-3-(4-pyrrolidin-1-ylmethylphenyl)acrylic Acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A reaction mixture of 0.3 g (1.15 mmol) of ethyl (E)-3-(4-pyrrolidin-1-ylmethylphenyl)acrylate and 0.4 g (9.53 mmol) of lithium hydroxide monohydrate in 20 mL of a 1:1 mixture of methanol, THF, and water is stirred for 48 hours at ambient temperature. Then the reaction mixture is evaporated down, the residue is diluted with water and acidified with hydrochloric acid. The mixture is evaporated down, combined with methanol and dichloromethane, filtered, and the filtrate is evaporated to dryness. Yield: 0.27 g, C14H17NO2 (M=231.29); calc.: molecular ion peak (M+H)+: 232; found: molecular ion peak (M+H)+: 232; Rf value: starting spot (silica gel, dichloromethane/methanol/ammonia (90:10:1)).

Workup

  1. customThen the reaction mixture is evaporated down
  2. additionthe residue is diluted with water
  3. customThe mixture is evaporated down
  4. filtrationfiltered
  5. customthe filtrate is evaporated to dryness

Sources & evidence

ORD record
ord-feda8eba49a24873898a6b34c5d872d2
Source dataset
uspto-grants-2009_09
Patent number
US07592373B2

Reaction notes

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