Dimethyl Sulfoxide → HCID 10802477, compound

HRID 976248Notes

Reaction equation

HRID 976248 reaction equation
[OH:1][C:2]1[C:3]2[CH:14]=[C:13]([O:15][CH3:16])[CH:12]=[CH:11][C:4]=2[S:5][C:6]=1[C:7]([O:9][CH3:10])=[O:8].CS(C)=O.CC(C)([O-])C.[K+].Br[CH2:28][C:29]#[N:30]>C(OCC)(=O)C>[CH3:10][O:9][C:7]([C:6]1[S:5][C:4]2[CH:11]=[CH:12][C:13]([O:15][CH3:16])=[CH:14][C:3]=2[C:2]=1[O:1][CH2:28][C:29]#[N:30])=[O:8]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 11534BromoacetonitrileHCID 23665647Potassium tert-butoxideHCID 54725366HCID 54725366, compound

Product 1

HCID 10802477HCID 10802477, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a room temperature solution of methyl 3-hydroxy-5-methoxybenzo[b]thiophene -2-carboxylate (1.00 g, 4.2 mmol) [Connor, et al., J. Med. Chem. 35:959 (1992)]in 20 mL of DMSO is added potassium t-butoxide (494 mg, 4.41 mmol) followed by bromoacetonitrile (878 μL, 12.58 mmol). The mixture is stirred at room temperature for 1.5 hours, then poured into ethyl acetate and 1N HC1. The organic layer is washed with 1N HCl, followed by several portions of brine, and dried over MgSO4. Filtration followed by removal of solvent in vacuo and recrystallization of the residue from ethyl acetate:hexane gives 413 mg. An additional crop of 112 mg can be obtained from the mother liquor, mp 159.5°-160° C.

Workup

  1. customTo a room temperature
  2. washThe organic layer is washed with 1N HCl
  3. dry with materialdried over MgSO4
  4. filtrationFiltration
  5. customfollowed by removal of solvent in vacuo and recrystallization of the residue from ethyl acetate
  6. customhexane gives 413 mg
  7. customAn additional crop of 112 mg can be obtained from the mother liquor, mp 159.5°-160° C.

Sources & evidence

ORD record
ord-2b4c18741f974424a9e951a9a68d4554
Source dataset
uspto-grants-1997_03
Patent number
US05612330

Reaction notes

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