Water → HCID 131735821, compound

HRID 2205974Notes

Reaction equation

HRID 2205974 reaction equation
[Br:1][C:2]1[CH:3]=[C:4](/[CH:15]=[CH:16]/[C:17]([OH:19])=O)[N:5]([CH2:7][O:8][CH2:9][CH2:10][Si:11]([CH3:14])([CH3:13])[CH3:12])[CH:6]=1.C(N(CC)CC)C.C1(P([N:41]=[N+:42]=[N-:43])(C2C=CC=CC=2)=O)C=CC=CC=1.O>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4](/[CH:15]=[CH:16]/[C:17]([N:41]=[N+:42]=[N-:43])=[O:19])[N:5]([CH2:7][O:8][CH2:9][CH2:10][Si:11]([CH3:14])([CH3:13])[CH3:12])[CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 131735822HCID 131735822, compound

Product 1

HCID 131735821HCID 131735821, compoundYield 94.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of (2E)-3-(4-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrol-2-yl)acrylic acid (4.5 g) in DMF (40 mL) was added a solution of triethylamine (2.0 mL) and diphenylphosphoryl azide (3.75 g) in DMF (5 mL) at 0° C., and the mixture was stirred at room temperature for 4 hr. The reaction mixture was added to water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (4.56 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-d7888804000448d9865eebd354a4e486
Source dataset
uspto-grants-2016_06
Patent number
US09371320B2

Reaction notes

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