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(Triphenylphosphoranylidene)acetaldehyde → (E)-3-(3-Methylbenzothiophen-2-yl)-2-propenal

HRID 377377
Notes
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Reaction equation

HRID 377377 reaction equation
[CH3:1][C:2]1[C:3]2[CH:12]=[CH:11][CH:10]=[CH:9][C:4]=2[S:5][C:6]=1[CH:7]=O.[CH:13]([CH:15]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:14]>C1(C)C=CC=CC=1>[CH3:1][C:2]1[C:3]2[CH:12]=[CH:11][CH:10]=[CH:9][C:4]=2[S:5][C:6]=1/[CH:7]=[CH:15]/[CH:13]=[O:14]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 75051(Triphenylphosphoranylidene)acetaldehydeHCID 5199183-Methylbenzo(b)thiophene-2-carboxaldehyde

Product 1

HCID 19358670(E)-3-(3-Methylbenzothiophen-2-yl)-2-propenalYield 52%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

3-Methylbenzo[b]thiophene-2-carboxaldehyde (4.2 g, 23.8 mmol) was dissolved in dry toluene (100 ml) and treated with (formylmethylene)triphenylphosphorane (7.35 g, 24.2 mmol). The reaction mixture was heated to 80° C. for 10 hours, allowed to cool and the residue was washed with 200 ml of hexane/Et2O 1/1 and then triturated with isopropyl ether to give pure title compound (2.5 g, 12.38 mmol, yield 52.0%), m.p.=90-92+ C.

Workup

  1. temperatureto cool
  2. washthe residue was washed with 200 ml of hexane/Et2O 1/1
  3. customtriturated with isopropyl ether

Sources & evidence

ORD record
ord-e24a02f6268443a78b230af36e4eaaed
Source dataset
uspto-grants-2000_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06025390

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes