Water → HCID 18947047, compound

HRID 1769080Notes

Reaction equation

HRID 1769080 reaction equation
[CH2:1]([Li])[CH2:2][CH2:3][CH3:4].[S:6]([N:16]1CC2=C[S:22][CH:23]=[C:18]2[CH2:17]1)([C:9]1[CH:15]=[CH:14][C:12]([CH3:13])=[CH:11][CH:10]=1)(=[O:8])=[O:7].IC.O>CCCCCC.O1CCCC1>[CH3:4][C:3]1[S:22][CH:23]=[C:18]2[CH2:17][N:16]([S:6]([C:9]3[CH:10]=[CH:11][C:12]([CH3:13])=[CH:14][CH:15]=3)(=[O:7])=[O:8])[CH2:1][C:2]=12

Participants

7

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 18947051HCID 18947051, compoundHCID 178418339Butyllithium

Product 1

HCID 18947047HCID 18947047, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

9.4 ml (15 mmol) of a 1.6M solution of butyllithium in hexane are added, at -70° C., to a solution of 3.5 g (12.5 mmol) of 5-tosyl-5,6-dihydro-4H-thieno[3,4-c]pyrrole in 40 ml of dry tetrahydrofuran; after 15 min, 1 ml (16 mmol) of iodomethane is added, the mixture is then stirred at room temperature for 30 min and poured into 200 ml of water. The precipitate formed is filtered and washed with hexane; after purification on silica gel using the 1/9 ethyl acetate/hexane eluent mixture, there are obtained 3.16 g of a white solid. Yield 86%. Melting point: 158°-160° C.

Workup

  1. customThe precipitate formed
  2. filtrationis filtered
  3. washwashed with hexane
  4. customafter purification on silica gel using the 1/9 ethyl acetate/hexane eluent mixture, there

Sources & evidence

ORD record
ord-14f58675bb4e4f8eb051be4ca542ce52
Source dataset
uspto-grants-1995_01
Patent number
US05380742

Reaction notes

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