Phosphorus oxychloride → methyl trans-3-(1-methyl-2-phenyl-1H-indol-3-yl)acrylate

HRID 547970

Reaction equation

HRID 547970 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.CO/[CH:19]=[CH:20]/[C:21]([O:23][CH3:24])=[O:22].P(Cl)(Cl)(Cl)=O>C(OCC)(=O)C.O.C(O)(=O)C>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](/[CH:19]=[CH:20]/[C:21]([O:23][CH3:24])=[O:22])=[C:3]1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

7

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 770951-Methyl-2-phenylindoleHCID 5323651Methyl 3-methoxyacrylate

Product 1

HCID 15732921methyl trans-3-(1-methyl-2-phenyl-1H-indol-3-yl)acrylateYield 76%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

1.04 g of 1-methyl-2-phenyl-1H-indol, 0.64 g of methyl trans-3-methoxyacrylate, 94.5 mg of water and 6 ml of glacial acetic acid were mixed, 124 mg of phosphorus oxychloride was added into the mixture at an inner temperature of 25° C., the added mixture was stirred for 7 hours at the same temperature to cause a reaction. After completion of the reaction, 30 mL of water was added dropwise into the reaction liquid, 50 mL of ethyl acetate was added and extraction treatment was conducted, and the resulting organic layer was subjected to concentration treatment. The resultant concentrated residue was purified by flash chromatography, to obtain 1.11 g of methyl trans-3-(1-methyl-2-phenyl-1H-indol-3-yl)acrylate (yellow solid). Yield: 76%.

Workup

  1. customa reaction
  2. additionwas added
  3. extractionextraction treatment
  4. concentrationthe resulting organic layer was subjected to concentration treatment
  5. customThe resultant concentrated residue was purified by flash chromatography

Sources & evidence

ORD record
ord-3468ebb38bf546dc893377d4f9cb30a2
Source dataset
uspto-grants-2011_05
Patent number
US07939674B2

Linked notes

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