Dichloromethane → HCID 70093703, compound

HRID 635376Notes

Reaction equation

HRID 635376 reaction equation
[C:1]1([S:7]([N:10]2[C:18]3[CH:17]=[CH:16][CH:15]=[C:14](C=O)[C:13]=3[CH:12]=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:21]([CH:26]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:23][CH2:24][CH3:25])=[O:22].Cl[CH2:47]Cl>>[CH2:24]([O:23][C:21](=[O:22])[CH:26]=[CH:47][C:14]1[CH:15]=[CH:16][CH:17]=[C:18]2[C:13]=1[CH:12]=[CH:11][N:10]2[S:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)(=[O:9])=[O:8])[CH3:25]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 10107997HCID 10107997, compound

Product 1

HCID 70093703HCID 70093703, compoundYield 100%

Procedure

A solution of 1-(benzenesulphonyl)-1H-indole-4-carboxaldehyde (2.0 g, 7 mmol) and (carbethoxymethylene)triphenylphosphorane (2.69 g,7.7 mmol) in anhydrous dichloromethane (50 ml) was heated to reflux for 3 h under a nitrogen atmosphere. The reaction was concentrated and purified by dry flash chromatography (dichloromethane) to give the title compound as a colourless solid (2.49 g, 100%). δH (360 MHZ, CDCl3), 1.34 (3H, t, J=7.2 Hz), 4.27 (2H, q, J=7.2 Hz), 6.51 (1H, d, J=17.2 Hz), 6.94 (1H, d, J=0.72 Hz), 7.32 (1H, t, J=7.9 Hz), 7.43-7.67 (4H, m), 7.67 (1H, d, J=3.6 Hz), 7.68-7.89 (2H, m), 7.94-8.03 (2H, m).

Workup

  1. temperatureto reflux for 3 h under a nitrogen atmosphere
  2. concentrationThe reaction was concentrated
  3. custompurified
  4. dry with materialby dry flash chromatography (dichloromethane)

Sources & evidence

ORD record
ord-d75ab8da10f14b7187b892f3f803b71d
Source dataset
uspto-grants-2001_02
Patent number
US06187805B1

Reaction notes

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