Methyl3-(2-cyanobenzo[b]thiophen-5-yl)acrylate → Methyl 2-cyanobenzo[b]thiophene-5-propionate

HRID 2288061Notes

Reaction equation

HRID 2288061 reaction equation
[C:1]([C:3]1[S:7][C:6]2[CH:8]=[CH:9][C:10]([CH:12]=[CH:13][C:14]([O:16][CH3:17])=[O:15])=[CH:11][C:5]=2[CH:4]=1)#[N:2]>C1COCC1.[Pd]>[C:1]([C:3]1[S:7][C:6]2[CH:8]=[CH:9][C:10]([CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15])=[CH:11][C:5]=2[CH:4]=1)#[N:2]

Participants

4

Reactant 1

HCID 54151697Methyl3-(2-cyanobenzo[b]thiophen-5-yl)acrylate

Product 1

HCID 18702952Methyl 2-cyanobenzo[b]thiophene-5-propionateYield 57.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Methyl 3-(2-cyanobenzo[b]thiophen-5-yl)acrylate (2.5 g) was hydrogenated in THF (20 ml) using 10% palladium on carbon (0.5 g) as catalyst until the majority of the starting material had disappeared by thin layer chromatography (silica plates eluting with ethyl acetate/hexane 1:4). The mixture was filtered and evaporated to give methyl 2-cyanobenzo[b]thiophene-5-propionate (1.45 g) contaminated with ~20% of starting material. Sodium hydroxide (0.23 g) was added to a mixture of this product (1.4 g) in THF (10 ml) and uater (3 ml) and the mixture was stirred for 2 hours. The mixture was adjusted to ~pH 5 with concentrated hydrochloric acid and concentrated by evaporation to remove the THF present.

Workup

  1. washhad disappeared by thin layer chromatography (silica plates eluting with ethyl acetate/hexane 1:4)
  2. filtrationThe mixture was filtered
  3. customevaporated

Sources & evidence

ORD record
ord-fdba02114225491ab8379d2be7f7e628
Source dataset
uspto-grants-2000_07
Patent number
US06087336

Reaction notes

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