Lithium hydroxide, monohydrate → HCID 68547903, compound

HRID 2243508Notes

Reaction equation

HRID 2243508 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]2[C:6]([S:13][CH2:14][C:15]#[N:16])=[C:7]([C:9](OC)=[O:10])[S:8][C:4]=2[CH:3]=1.O.[OH-].[Li+]>CN(C=O)C.Cl.C(OCC)(=O)C>[Cl:1][C:2]1[CH:18]=[CH:17][C:5]2[C:6]3[S:13][C:14]([C:15]#[N:16])=[C:9]([OH:10])[C:7]=3[S:8][C:4]=2[CH:3]=1

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 68547563HCID 68547563, compound

Product 1

HCID 68547903HCID 68547903, compoundYield 43.5%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of methyl 6-chloro-3-[(cyanomethyl)thio]-1-benzothiophene-2-carboxylate (1.01 g, 3.4 mmol) in DMF (20 mL) was cooled to 0° C., and lithium hydroxide hydrate (171 mg, 1.2 eq) was added in a single portion. After 1h, the solution was warmed to room temperature and stirred for an additional hour. The reaction solution was diluted with aq. hydrochloric acid and ethyl acetate. The organic layer was washed with water and brine, dried, filtered, evaporated, and recrystallized (EtOH) to provide 6-chloro-3-hydroxythieno[3,2-b][1]benzothiophene-2-carbonitrile (393 mg, 43%) as an off-white solid.

Workup

  1. washThe organic layer was washed with water and brine
  2. customdried
  3. filtrationfiltered
  4. customevaporated
  5. customrecrystallized (EtOH)

Sources & evidence

ORD record
ord-576f26996dff4bc296cd700f91e50a67
Source dataset
uspto-grants-2010_03
Patent number
US07674822B2

Reaction notes

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