Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → HCID 13707694, compound

HRID 878979Notes

Reaction equation

HRID 878979 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH:10]=O)[CH:8]=2)[CH:3]=[CH:2]1.[CH3:12][O:13][C:14]([CH:16]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:15]>O1CCCC1>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7](/[CH:10]=[CH:16]/[C:14]([O:13][CH3:12])=[O:15])[CH:8]=2)[CH:3]=[CH:2]1

Participants

4

Reactant 2

HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 27734351H-Indole-6-carboxaldehyde

Product 1

HCID 13707694HCID 13707694, compoundYield 72.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of indole-6-carboxaldehyde (499 mg) in tetrahydrofuran (20 mL), methyl (triphenylphosphoranylidene) acetate (2.5 g) was added at room temperature, and then the reaction mixture was subjected to microwave irradiation at 200° C. for 20 minutes. The reaction mixture was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography to give the titled compound (501 mg) as a yellow solid.

Workup

  1. customirradiation at 200° C. for 20 minutes
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-2924c33d69af42f28d73eb464f8ec265
Source dataset
uspto-grants-2015_03
Patent number
US08987473B2

Reaction notes

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