N-Methoxy-N-methylundec-10-enamide → HCID 53810906, compound

HRID 128794Notes

Reaction equation

HRID 128794 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]=[CH:9][O:10][CH3:11].C([Li])CCC.CON(C)[C:20](=[O:31])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH:29]=[CH2:30]>C1COCC1.CCCCCC>[CH3:11][O:10][CH:9]=[CH:8][C:3]1[CH:4]=[CH:5][C:6]([C:20](=[O:31])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH:29]=[CH2:30])=[CH:7][CH:2]=1

Participants

6

Reactant 3

HCID 294216N-Methoxy-N-methylundec-10-enamideHCID 54035192HCID 54035192, compoundHCID 178418339Butyllithium

Product 1

HCID 53810906HCID 53810906, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

To a solution of 1-bromo-(2-methoxyethenyl)benzene (2.13 g) in THF (20 ml) at -78° is added dropwise a 2.5M solution of n-butyllithium in hexane (4.2 ml). The temperature is not allowed to rise above -55°. After 90 min, a solution of N-methoxy-N-methyl-10-undecenamide (2.3 g) in THF (5 ml) is added dropwise, and the mixture stirred an additional 60 min at -78°. The mixture is not allowed to warm, but is immediately quenched by the addition of 10% aqueous citric acid. The mixture is extracted with dichloromethane, and the extracts are dried, filtered, and concentrated. The crude product is chromatographed with 1:1 dichloromethanehexane, to provide 1-(4-(2-methoxyethenyl)phenyl)-10-undecen-1-one as a colorless solid.

Workup

  1. customto rise above -55°
  2. temperatureto warm
  3. customis immediately quenched by the addition of 10% aqueous citric acid
  4. extractionThe mixture is extracted with dichloromethane
  5. customthe extracts are dried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product is chromatographed with 1:1 dichloromethanehexane

Sources & evidence

ORD record
ord-c05f9d319c7a4dc6b5b23f58dc5e8edd
Source dataset
uspto-grants-1995_11
Patent number
US05464865

Reaction notes

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