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6-Isopropyl-4,4-dimethyl-1-ethyl-1,2,3,4-tetrahydro-quinoline-8-carbaldehyde → 6-Isopropyl-4,4-dimethyl-1-n-propyl-1,2,3,4-tetrahydro-quinoline-8-carbaldehyde

HRID 1582081
Notes
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Reaction equation

HRID 1582081 reaction equation
[CH:1]([C:4]1[CH:5]=[C:6]2[C:11](=[C:12]([CH:14]=[O:15])[CH:13]=1)[N:10]([CH2:16][CH3:17])[CH2:9][CH2:8][C:7]2([CH3:19])[CH3:18])([CH3:3])[CH3:2].[CH3:20][Mg]Br>C1COCC1>[CH:1]([C:4]1[CH:5]=[C:6]2[C:11](=[C:12]([CH:14]=[O:15])[CH:13]=1)[N:10]([CH2:16][CH2:17][CH3:20])[CH2:9][CH2:8][C:7]2([CH3:19])[CH3:18])([CH3:2])[CH3:3]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 227198126-Isopropyl-4,4-dimethyl-1-ethyl-1,2,3,4-tetrahydro-quinoline-8-carbaldehyde2×HCID 178418573HCID 178418573, compound

Product 1

HCID 867594426-Isopropyl-4,4-dimethyl-1-n-propyl-1,2,3,4-tetrahydro-quinoline-8-carbaldehyde

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a solution of 6-isopropyl-4,4-dimethyl-1-ethyl-1,2,3,4-tetrahydro-quinoline-8-carbaldehyde (Intermediate 7, 2.00 g, 9.00 mmol) and 35 ml of anhydrous THF under argon at −78° C. was slowly added 3 M solution of methyl magnesium bromide in THF (7.5 ml, 22.5 mmol). The resulting solution was stirred at −78° C. for 45 minutes. The reaction was quenched with saturated NH4Cl and the product was extracted with diethyl ether. The organic extract was washed with water, and brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by column chromatography using 5% ethyl acetate in hexane to yield the title compound as light yellow oil.

Workup

  1. customat −78° C.
  2. customThe reaction was quenched with saturated NH4Cl
  3. extractionthe product was extracted with diethyl ether
  4. extractionThe organic extract
  5. washwas washed with water, and brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-3a784779a48c4c6ea130a139d435c93d
Source dataset
uspto-grants-2004_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06734193B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes