HCID 58545553, compound → HCID 58545574, compound

HRID 71992Notes

Reaction equation

HRID 71992 reaction equation
CON(C)[C:4]([C:6]1[S:10][CH:9]2[CH:11]=[CH:12][S:13][CH:8]2[CH:7]=1)=[O:5].[CH3:15][Mg]Br>C1COCC1>[S:10]1[C:6]([C:4](=[O:5])[CH3:15])=[CH:7][CH:8]2[S:13][CH:12]=[CH:11][CH:9]12

Participants

4

Reactant 2

HCID 58545553HCID 58545553, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 58545574HCID 58545574, compoundYield 124.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3a,6a-Dihydro-thieno[3,2-b]thiophene-2-carboxylic acid methoxy-methyl-amide (1.955 g, 8.60 mmol) was dissolved in THF. The stirred solution was cooled to 0° C. before methylmagnesium bromide (1.4 M in PhMe, 8.6 mL, 12.04 mmol) was added. The reaction was allowed to gradually warm to RT o/n, then it was quenched by addition of 10% HCl. The aqueous phase was extracted with diethyl ether. The organic phase was washed with brine then dried over MgSO4, filtered and concentrated to afford the title compound (1.98 g, 80%).

Workup

  1. additionwas added
  2. customwas quenched by addition of 10% HCl
  3. extractionThe aqueous phase was extracted with diethyl ether
  4. washThe organic phase was washed with brine
  5. dry with materialthen dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-47dd8055b5d549b4a287e9bd0d63a363
Source dataset
uspto-grants-2014_09
Patent number
US08822430B2

Reaction notes

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