Hydrochloric Acid → 1-{[(Benzyloxy)imino]methyl}cyclopentane-1-carboxylic acid

HRID 2055166Notes

Reaction equation

HRID 2055166 reaction equation
C[O:2][C:3]([C:5]1([CH:10]=[N:11][O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:9][CH2:8][CH2:7][CH2:6]1)=[O:4].[OH-].[Na+].Cl>C1COCC1.CO.O>[CH2:13]([O:12][N:11]=[CH:10][C:5]1([C:3]([OH:4])=[O:2])[CH2:9][CH2:8][CH2:7][CH2:6]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 866064701-(Benzyloxyimino-methyl)-cyclopentanecarboxylic acid methyl ester

Product 1

HCID 714169871-{[(Benzyloxy)imino]methyl}cyclopentane-1-carboxylic acid

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1-(benzyloxyimino-methyl)-cyclopentanecarboxylic acid methyl ester (2.26 g, 8.65 mmol) and sodium hydroxide (1.0 g, 25.9 mmol) in THF (15 mL), methanol (15 mL) and water (5 mL) was stirred at room temperature for 18 h. The reaction mixture was acidified to pH 4 with 3N aqueous HCl and was extracted with dichloromethane (50 mL×3). The combined organic layers were dried (MgSO4) and were evaporated in vacuo to yield the title compound as a pale yellow oil. (1.91 g, 89%). MH+248.

Workup

  1. extractionwas extracted with dichloromethane (50 mL×3)
  2. dry with materialThe combined organic layers were dried (MgSO4)
  3. customwere evaporated in vacuo

Sources & evidence

ORD record
ord-d2e6b50150e346809d5cdd9ffbd0b5af
Source dataset
uspto-grants-2008_02
Patent number
US07332485B2

Reaction notes

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