Benzaldehyde → HCID 641422, compound

HRID 2306780Notes

Reaction equation

HRID 2306780 reaction equation
[CH3:1][CH2:2][O:3][C:4](/[CH:6]=[CH:7]/[CH2:8]P(OCC)(OCC)=O)=[O:5].C([Li])CCC.[CH:22](=O)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[Cl-].[NH4+]>O1CCCC1>[C:23]1(/[CH:22]=[CH:8]/[CH:7]=[CH:6]/[C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 25517Ammonium ChlorideHCID 5365783Triethyl 4-phosphonocrotonate, mixture of isomersHCID 178418339Butyllithium

Product 1

HCID 641422HCID 641422, compoundYield 82.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 16 ml (72 mmol) of triethyl 4-phosphonocrotonate in anhydrous tetrahydrofuran (100 ml) was added 43 ml (69 mmol) of a 1.6 M n-butyllithium solution dropwise with stirring in an ice-salt bath under nitrogen, and the mixture was stirred for 30 minutes. Then, 5.0 ml (49 mmol) of benzaldehyde was added dropwise to this reaction mixture over about 5 minutes, and the resultant mixture was stirred for 10 minutes in the ice-salt bath and for an additional 3 hours at room temperature. A saturated aqueous solution of ammonium chloride was added to the reaction mixture to conduct extraction with ether. An organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure, and the resultant crude oil (15.9 g) was purified by chromatography on silica gel, thereby obtaining 8.14 g (yield: 82%) of ethyl 5-phenylpenta-(2E,4E)-dienoate.

Workup

  1. stirringthe mixture was stirred for 30 minutes
  2. extractionextraction with ether
  3. dry with materialAn organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customthe resultant crude oil (15.9 g) was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-093096b4262f4d94bd1a4e12bdd918c4
Source dataset
uspto-grants-2004_12
Patent number
US06828316B2

Reaction notes

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