Lithium Hydroxide → HCID 90025778, compound

HRID 1054975Notes

Reaction equation

HRID 1054975 reaction equation
CC1C=C(C)C=C(C)C=1S([O-])(=O)=O.[NH2:14][N:15]1[C:20]([CH3:21])=[C:19]([Cl:22])[CH:18]=[C:17]([CH3:23])[C:16]1=[NH2+:24].[CH:25]([CH:27]1[CH2:29][CH:28]1[C:30]([O:32]CC)=[O:31])=O.[OH-].[K+].[Li+].[OH-]>CO.O1CCCC1>[Cl:22][C:19]1[CH:18]=[C:17]([CH3:23])[C:16]2[N:15]([N:14]=[C:25]([CH:27]3[CH2:29][CH:28]3[C:30]([OH:32])=[O:31])[N:24]=2)[C:20]=1[CH3:21]

Participants

7

Reactant 4

HCID 3939Lithium HydroxideHCID 14797Potassium HydroxideHCID 89334Ethyl 2-formylcyclopropanecarboxylateHCID 178425975HCID 178425975, compound

Product 1

HCID 90025778HCID 90025778, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

1-Amino-5-chloro-3,6-dimethylpyridin-2(1H)-iminium 2,4,6-trimethylbenzenesulfonate (100 mg, 269 μmol, Eq: 1.00) was added to a solution of ethyl 2-formylcyclopropanecarboxylate (38.2 mg, 269 μmol, Eq: 1.00) in methanol (2 ml). 2 N KOH aq (200 μl, 400 μmol, Eq: 1.49) was added and the yellow mixture was stirred for 1 h at room temperature under air. 1 N LiOH aq (4 mL, 4 mmol, Eq: 14.9) and tetrahydrofuran (8 ml) were added and the mixture was stirred for 30 min at room temperature. Volatile organic solvents were evaporated, water (10 ml) was added and the mixture was washed with diethyl ether (10 ml). The aqueous phase was acidified with 2 N HCl aq and then extracted with ethyl acetate (3×10 ml). The combined organic layers were dried over sodium sulfate and then concentrated to give the desired product (70 mg, 98%) as a white solid. MS: m/z=266.1 (M+H+)

Workup

  1. stirringthe mixture was stirred for 30 min at room temperature
  2. customVolatile organic solvents were evaporated
  3. additionwater (10 ml) was added
  4. washthe mixture was washed with diethyl ether (10 ml)
  5. extractionextracted with ethyl acetate (3×10 ml)
  6. dry with materialThe combined organic layers were dried over sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-f44cbd1e07ba413897150122e3c65780
Source dataset
uspto-grants-2016_07
Patent number
US09394311B2

Reaction notes

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