Water → HCID 68540610, compound

HRID 2243478Notes

Reaction equation

HRID 2243478 reaction equation
C[C:2](C)([O-:4])C.[Na+].[C:7]([O:11][CH3:12])(=[O:10])[CH2:8][SH:9].COC([C:17]1[C:18]2[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=2[S:20][C:21]=1Cl)=O.O>CN(C=O)C>[CH3:12][O:11][C:7]([C:8]1[S:9][C:17]2[C:18]3[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=3[S:20][C:21]=2[C:2]=1[OH:4])=[O:10]

Participants

6

Reactant 4

HCID 962WaterHCID 16907Methyl ThioglycolateHCID 23676156Sodium t-butoxideHCID 68544260HCID 68544260, compound

Product 1

HCID 68540610HCID 68540610, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium tert-butoxide (360 mg, 3.7 mmol, 3.3 equiv) was added to a solution of methyl thioglycolate (0.110 ml, 1.23 mmol, 1.1 equiv) in DMF (10 ml). 2-chloro-benzo[b]thiophene-3-carboxylic acid methyl ester (235 mg, 1.12 mmol, 1 equiv, available from Maybridge) was then added and the mixture became orange. When no starting material was observed by TLC, water was added followed by extraction with EtOAc. Purification by column chromatography yielded 162 mg (61%) of 1-hydroxy-3,8-dithia-cyclopenta[a]indene-2-carboxylic acid methyl ester as an orange solid.

Workup

  1. additionwas added
  2. extractionfollowed by extraction with EtOAc
  3. customPurification by column chromatography

Sources & evidence

ORD record
ord-259fd44b8a534d28a926aabbb9d2f99f
Source dataset
uspto-grants-2010_03
Patent number
US07674822B2

Reaction notes

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