Borane;tetrahydrofuran → HCID 18376695, compound

HRID 844168Notes

Reaction equation

HRID 844168 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][CH:7]=[C:8]([CH2:11][C:12]#[N:13])[C:9]=1[Cl:10])=[O:4].B.C1COCC1>C1COCC1>[CH3:1][O:2][C:3]([C:5]1[S:6][CH:7]=[C:8]([CH2:11][CH2:12][NH2:13])[C:9]=1[Cl:10])=[O:4]

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 18376874HCID 18376874, compound

Product 1

HCID 18376695HCID 18376695, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2-Methoxycarbonyl-3-chloro-4-cyanomethylthiophene (2 g, 9.27 mmol) was dissolved in THF (100 mL) and BH3-THF (18.6 mL of a 1 M solution in THF, 18.6 mmol) was added. After stirring for 16 hours at ambient temperature, the reaction was quenched with water followed by 1 M NaOH. Potassium carbonate was added to afford two layers. The organic layer was separated and concentrated in vacuo to afford 2-methoxycarbonyl-3-chloro-4-(2-aminoethyl)thiophene.

Workup

  1. customthe reaction was quenched with water
  2. additionPotassium carbonate was added
  3. customto afford two layers
  4. customThe organic layer was separated
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-98052b51312c42f794004da4c5fe7d7e
Source dataset
uspto-grants-2002_04
Patent number
US06380221B1

Reaction notes

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