Ammonium Chloride → methyl (E,E,E)-7-[1-(1-methylethyl)-1,2,3,4-tetrahydroquinolin-6-yl]-3-methylocta-2,4,6-trienoate

HRID 1596548Notes

Reaction equation

HRID 1596548 reaction equation
[Na].C[CH2:3][O:4][C:5](/[CH:7]=[C:8](/[CH2:10]P(OCC)(OCC)=O)\[CH3:9])=[O:6].[CH3:19][CH:20]([N:22]1[C:31]2[C:26](=[CH:27][C:28](/[C:32](/[CH3:36])=[CH:33]/[CH:34]=O)=[CH:29][CH:30]=2)[CH2:25][CH2:24][CH2:23]1)[CH3:21].[Cl-].[NH4+]>CO>[CH3:21][CH:20]([N:22]1[C:31]2[C:26](=[CH:27][C:28](/[C:32](/[CH3:36])=[CH:33]/[CH:34]=[CH:10]/[C:8](/[CH3:9])=[CH:7]/[C:5]([O:4][CH3:3])=[O:6])=[CH:29][CH:30]=2)[CH2:25][CH2:24][CH2:23]1)[CH3:19]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 5360545Sodium2×HCID 6000084Ethyl 4-(diethoxyphosphoryl)-3-methylbut-2-enoateHCID 10490444(E)-3-[1-(1-methylethyl)-1,2,3,4-tetrahydroquinolin-6-yl]-2-butenal

Product 1

HCID 10569101methyl (E,E,E)-7-[1-(1-methylethyl)-1,2,3,4-tetrahydroquinolin-6-yl]-3-methylocta-2,4,6-trienoateYield 59.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

56 mg (2.46 mmol) of metallic sodium was added to methanol to prepare a meethanolic solution or sodium meethoxide. This solution was concentrated in a vacuum and suspended in N,N-dimethylformamide, followed by the addition of 560 mg (2.14 mmol) of triethyl 3-methyl-4-phosphonocrotonate under cooling with ice. After 30 minutes, 400 mg (1.64 mmol) of (E)-3-[1-(1-methylethyl)-1,2,3,4-tetrahydroquinolin-6-yl]-2-butenal was added to the mixture obtained above. The mixture thus obtained was stirred for one hour, followed by the addition of an aqueous solution of ammonium chloride. The obtained mixture was extracted with ethyl acetate. The organic phase was dried over anhydrous magnesium sulfate and concentrated in a vacuum. The obtained residue was purified by silica gel column chromatography (15% ethyl acetate/n-hexane) to give 330 mg of the title compound as a reddish-brown oil.

Workup

  1. concentrationThis solution was concentrated in a vacuum
  2. temperatureunder cooling with ice
  3. customobtained above
  4. customThe mixture thus obtained
  5. extractionThe obtained mixture was extracted with ethyl acetate
  6. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  7. concentrationconcentrated in a vacuum
  8. customThe obtained residue was purified by silica gel column chromatography (15% ethyl acetate/n-hexane)

Sources & evidence

ORD record
ord-bd705cba3dbc4f8ab10c16429632d725
Source dataset
uspto-grants-2001_09
Patent number
US06291508B1

Reaction notes

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