Methanol → HCID 13837141, compound

HRID 2080016Notes

Reaction equation

HRID 2080016 reaction equation
CC(C)([O-])C.[K+].[N+:7]([C:10]1[S:11][CH:12]=[CH:13][CH:14]=1)([O-:9])=[O:8].[CH:15](Cl)([Cl:17])[Cl:16].CO>CN(C)C=O.[Cl-].[Na+].O.C(O)(=O)C>[Cl:16][CH:15]([Cl:17])[C:14]1[CH:13]=[CH:12][S:11][C:10]=1[N+:7]([O-:9])=[O:8]

Participants

8

Reactant 4

HCID 887MethanolHCID 6212ChloroformHCID 11866Thiophene, 2-nitro-HCID 23665647Potassium tert-butoxide

Product 1

HCID 13837141HCID 13837141, compoundYield 94%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 6228DimethylformamideSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of potassium tert-butoxide (23.0 mL, 1.0M tetrahydrofuran solution, 23.2 mmol) in N,N-dimethyl formamide (20 mL) were added a mixture solution of 2-nitro-thiophene (1.00 g, 7.74 mmol) in chloroform (682 μl, 8.51 mmol) and N,N-dimethylformamide (2 mL) dropwise at −78° C., the solution was stirred for 5 minutes, and then, methanol and acetic acid were added at 0° C. Brine was added to the reaction solution, which was then extracted with ethyl acetate. The solvent was evaporated in vacuo, the residue was purified by silica gel column chromatography (hexane:ethyl acetate=20:1), and the title compound (1.54 g, 7.26 mmol, 94%) was obtained as a light brown solid.

Workup

  1. extractionwas then extracted with ethyl acetate
  2. customThe solvent was evaporated in vacuo
  3. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=20:1)

Sources & evidence

ORD record
ord-1dddabca55764c5ba2d8b4d0e8d08205
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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