Dimethylformamide → HCID 20739786, compound

HRID 392008Notes

Reaction equation

HRID 392008 reaction equation
[CH2:1]([N:3]1[C:15]2[CH:14]=[CH:13][C:12]([CH:16]=O)=[CH:11][C:10]=2[C:9]2[C:4]1=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH3:2].[CH3:18]N(C)C=O.CO.C[O-].[Na+]>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O>[CH2:1]([N:3]1[C:15]2[CH:14]=[CH:13][C:12]([CH:16]=[CH2:18])=[CH:11][C:10]=2[C:9]2[C:4]1=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH3:2]

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 820559-ethyl-9H-carbazole-3-carbaldehydeHCID 23694274Sodium methanolate methanol

Product 1

HCID 20739786HCID 20739786, compound

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 962WaterSolvent

Conditions

Temperature
-5 °C

Procedure

A three-necked flask having an inner volume of 500 ml equipped with a thermometer and a reflux condenser was charged with 22.3 g (0.1 mol) of N-ethylcarbazole-3-carboxaldehyde, 39 g (0.11 mol) of methyltriphenyl phosphonium bromide and 150 ml of N,N-dimethylformamide. This mixture was cooled by an ice-methanol bath to −5° C. under nitrogen gas stream while stirring the mixture by a magnetic stirring bar. To the mixture was gradually added 30 ml of 28% sodium methoxide methanol solution dropwise while maintaining the temperature of the mixture below 5° C. Then, the resultant mixture was stirred for 1 hour at 10° C., stirred for 2 hours at room temperature, poured into 3 L of cold water to deposite a crude solid, and filtered to obtain the crude solid. The crude solid was washed with water and dried, and the residue was purified by a silica gel column chromatography (dissolution medium: hexane/ethyl acetate=5/1). The dissolution medium was distilled off from the fraction containing the desired product and the resultant oil was subjected to crystallization using iso-propanol, to obtain 21 g of N-ethyl-3-vinylcarbazole as a crystal.

Workup

  1. customA three-necked flask having
  2. customan inner volume of 500 ml equipped with a thermometer and a reflux condenser
  3. temperaturewhile maintaining the temperature of the mixture below 5° C
  4. stirringstirred for 2 hours at room temperature
  5. filtrationfiltered
  6. customto obtain the crude solid
  7. washThe crude solid was washed with water
  8. customdried
  9. customthe residue was purified by a silica gel column chromatography (dissolution medium: hexane/ethyl acetate=5/1)
  10. distillationThe dissolution medium was distilled off from the fraction
  11. additioncontaining the desired product
  12. customthe resultant oil was subjected to crystallization

Sources & evidence

ORD record
ord-f021ca1ab3d54c40aa27f67950ec0d72
Source dataset
uspto-grants-2004_10
Patent number
US06800379B2

Reaction notes

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