Hydrochloric Acid → HCID 59129303, compound

HRID 1908374Notes

Reaction equation

HRID 1908374 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]3([C:13]([O:15]C)=[O:14])[CH2:12][CH2:11]3)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[Li+].[OH-].Cl>CO.O>[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]3([C:13]([OH:15])=[O:14])[CH2:12][CH2:11]3)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 59129295HCID 59129295, compound

Product 1

HCID 59129303HCID 59129303, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
45 °C

Procedure

To a solution of methyl 1-(1H-indol-5-yl)cyclopropanecarboxylate (1.74 g, 8 mmol) in CH3OH (50 mL) and water (20 mL) was added LiOH (1.7 g, 0.04 mol). The mixture was heated at 45° C. for 3 hr. Water was added and the mixture was acidified with concentrated HCl to pH 3 before being extracted with EtOAc (20 mL×3). The organic layers were dried over anhydrous Na2SO4 and evaporated to give 1-(1H-indol-5-yl)cyclopropanecarboxylic acid (1.4 g, 87%). 1H NMR (300 MHz, DMSO-d6) 7.43 (s, 1H), 7.30-7.26 (m, 2H), 7.04 (dd, J=1.5, 8.4 Hz, 1H), 6.35 (s, 1H), 1.45-1.41 (m, 2H), 1.14-1.10 (m, 2H).

Workup

  1. extractionbefore being extracted with EtOAc (20 mL×3)
  2. dry with materialThe organic layers were dried over anhydrous Na2SO4
  3. customevaporated

Sources & evidence

ORD record
ord-60337e6b3acb4dc3a83a5e2b7462415b
Source dataset
uspto-grants-2013_12
Patent number
US08598181B2

Reaction notes

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