Isobutyraldehyde → HCID 62549883, compound

HRID 562209Notes

Reaction equation

HRID 562209 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:7][CH2:8][NH2:9])[S:5][CH:6]=1.[CH3:10][CH:11](C)[CH:12]=O.[BH4-].[Na+].CCOC(C)=O>C(Cl)Cl.CO.C(O)(=O)C.[Cl-].[Na+].O>[Br:1][C:2]1[CH:3]=[C:4]([CH2:7][CH2:8][NH:9][CH:11]([CH3:12])[CH3:10])[S:5][CH:6]=1

Participants

9

Reactant 4

HCID 6561IsobutyraldehydeHCID 8857Ethyl AcetateHCID 4311764Sodium borohydrideHCID 150366152-(4-Bromothiophen-2-yl)ethan-1-amine

Product 1

HCID 62549883HCID 62549883, compoundYield 67.2%

Reagents, catalysts & solvents 4

HCID 176Acetic AcidCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of [2-(4-bromo-2-thienyl)ethyl]amine (100 mg, 0.48 mmol) in DCM (2.0 mL) and MeOH (1.0 mL) was added acetic acid (3 drops) and 2-methylpropanal (105 mg, 1.44 mmol). The reaction was stirred overnight at room temperature before addition of Sodium borohydride (53.3 mg, 1.44 mmol). Reaction run for 1 h and then treated with EtOAc and brine. Organic layers were then dried and concentrated to give 80 mg of [2-(4-bromo-2-thienyl)ethyl](1-methylethyl)amine (64%).

Workup

  1. customReaction run for 1 h
  2. customOrganic layers were then dried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-8ff05d5d77094f56b4dd55c48cfb9a3b
Source dataset
uspto-grants-2011_11
Patent number
US08063071B2

Reaction notes

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