Hexane → HCID 53239248, compound

HRID 2205973Notes

Reaction equation

HRID 2205973 reaction equation
[CH3:1][Si:2]([CH3:15])([CH3:14])[CH2:3][CH2:4][O:5][CH2:6][N:7]1[CH:11]=[CH:10][CH:9]=[C:8]1[CH:12]=[O:13].C1C(=O)N([Br:23])C(=O)C1.CCCCCC>C1COCC1>[Br:23][C:10]1[CH:9]=[C:8]([CH:12]=[O:13])[N:7]([CH2:6][O:5][CH2:4][CH2:3][Si:2]([CH3:15])([CH3:14])[CH3:1])[CH:11]=1

Participants

5

Reactant 3

HCID 8058HexaneHCID 67184N-bromobutanimideHCID 132114621-{[2-(Trimethylsilyl)ethoxy]methyl}-1H-pyrrole-2-carbaldehyde

Product 1

HCID 53239248HCID 53239248, compoundYield 85.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrole-2-carbaldehyde (4.51 g) in THF (79 mL) was added NBS (4.27 g) at −20° C., and the mixture was stirred at 0° C. for 6 hr. To the reaction mixture was added hexane (240 mL), the precipitate was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (5.2 g).

Workup

  1. customthe precipitate was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-44539a3692b74b8bae538d5c617848c8
Source dataset
uspto-grants-2016_06
Patent number
US09371320B2

Reaction notes

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