HCID 67255399, compound → HCID 67257627, compound

HRID 2371051Notes

Reaction equation

HRID 2371051 reaction equation
[CH3:1][C:2]1[C:3]2[C:9](=O)[CH2:8][CH:7]([CH2:11][N+:12]([O-:14])=[O:13])[C:4]=2[S:5][CH:6]=1>C1COCC1>[CH3:1][C:2]1[C:3]2[CH2:9][CH2:8][CH:7]([CH2:11][N+:12]([O-:14])=[O:13])[C:4]=2[S:5][CH:6]=1

Participants

3

Reactant 1

HCID 67255399HCID 67255399, compound

Product 1

HCID 67257627HCID 67257627, compoundYield 56.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-methyl-6-(nitromethyl)-5,6-dihydro-4H-cyclopenta[b]thiophen-4-one (9.5 g) in 13H3.THF (400 mL) was stirred at room temperature overnight. TLC analysis indicated the consumption of starting material. The reaction mixture was acidified to pH 2 with 10% HCl and stirred for 2 h. The mixture was extracted with EtOAc (100 mL×3). The combined organic phase was dried with Na2SO4, and concentrated in vacuo. The crude product was purified by flash column chromatography to afford 5 g of title compound (yield: 56.4%).

Workup

  1. customthe consumption of starting material
  2. extractionThe mixture was extracted with EtOAc (100 mL×3)
  3. dry with materialThe combined organic phase was dried with Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by flash column chromatography

Sources & evidence

ORD record
ord-b5f9b073200d470b8429516d95c01ab3
Source dataset
uspto-grants-2014_04
Patent number
US08710245B2

Reaction notes

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