Methyl Thioglycolate → Methyl 5-methoxybenzo[b]thiophene-2-carboxylate

HRID 493177Notes

Reaction equation

HRID 493177 reaction equation
[C:1]([O:5][CH3:6])(=[O:4])[CH2:2][SH:3].[H-].[Na+].F[C:10]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][C:11]=1[CH:12]=O>CS(C)=O>[CH3:6][O:5][C:1]([C:2]1[S:3][C:10]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][C:11]=2[CH:12]=1)=[O:4]

Participants

5

Reactant 3

HCID 16907Methyl ThioglycolateHCID 24758Sodium hydrideHCID 27348722-Fluoro-5-methoxybenzaldehyde

Product 1

HCID 23261726Methyl 5-methoxybenzo[b]thiophene-2-carboxylateYield 13.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of methyl thioglycolate (0.647 mL, 7.14 mmol, 1.1 eq.) in 14 mL of DMSO was added NaH 50% (0.405 g, 10.1 mmol, 1.56 eq.) and the mixture was stirred for 5 Min., before 2-fluoro-5-methoxybenzaldehyde (1.00 g, 6.49 mmol) was added (strongly exothermic). When the internal temperature had reached again 25° C., the reaction mixture was poured onto crashed ice and the precipitate filtered off and dried to obtain 0.199 g of the title compound as off-white solid.

Workup

  1. customhad reached again 25° C.
  2. additionthe reaction mixture was poured
  3. filtrationthe precipitate filtered off
  4. customdried

Sources & evidence

ORD record
ord-123fa6c6fa0c4864ac26cdcfdc882ad1
Source dataset
uspto-grants-2009_05
Patent number
US07534788B2

Reaction notes

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