Benzaldehyde → Cinnamoylbenzene

HRID 618976Notes

Reaction equation

HRID 618976 reaction equation
[CH:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O-][CH2:10][CH3:11].[Na+]>C1COCC1>[C:2]1([CH:10]=[CH:11][C:1]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:8])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 240BenzaldehydeHCID 2723922Sodium ethoxide

Product 1

HCID 7189Cinnamoylbenzene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 50 mg (0.47 mmol) benzaldehyde and 100 mg (0.047 mmol) Rink amide resin bound compound 1 in 5 mL THF, 12 μL 2M sodium ethoxide was added. It was shaken at room temperature for 2 hours. The resulting Resin bound compound 2 was collected in a 3 mL filtering column and washed with water (3×2 mL), DMF (2×2 mL) and methylene chloride (3×2 mL). After drying under vacuum, 5 mg Resin bound compound 2 was treated with 1.5 mL 5% trifluoroacetic acid in methylene chloride for 20 minutes. The solid was filtered off and washed with 1 mL methylene chloride, combined methylene chloride solution was concentrated and dried under vacuum to give 0.5 mg product 3. MS m/z252 (M+ +1). ##STR55##

Workup

  1. additionwas added
  2. customwas collected in a 3 mL
  3. filtrationfiltering column
  4. washwashed with water (3×2 mL), DMF (2×2 mL) and methylene chloride (3×2 mL)
  5. dry with materialAfter drying under vacuum, 5 mg Resin
  6. additionwas treated with 1.5 mL 5% trifluoroacetic acid in methylene chloride for 20 minutes
  7. filtrationThe solid was filtered off
  8. washwashed with 1 mL methylene chloride
  9. concentrationwas concentrated
  10. customdried under vacuum

Sources & evidence

ORD record
ord-e5c4f5ad9d5442ae89b5cc90b850a76a
Source dataset
uspto-grants-1999_09
Patent number
US05958792

Reaction notes

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