Diethyl Ether → HCID 10494674, compound

HRID 278027Notes

Reaction equation

HRID 278027 reaction equation
C(OCC)C.[C:6]([C:10]1[CH:15]=[CH:14][C:13]([Mg]Br)=[CH:12][CH:11]=1)([CH3:9])([CH3:8])[CH3:7].[CH:18]([C:21]1[CH:22]=[C:23]2[C:28](=[CH:29][CH:30]=1)[N:27]=[CH:26][CH:25]=[CH:24]2)([CH3:20])[CH3:19]>O1CCCC1>[C:6]([C:10]1[CH:15]=[CH:14][C:13]([C:26]2[CH:25]=[CH:24][C:23]3[C:28](=[CH:29][CH:30]=[C:21]([CH:18]([CH3:20])[CH3:19])[CH:22]=3)[N:27]=2)=[CH:12][CH:11]=1)([CH3:9])([CH3:8])[CH3:7]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 672856-IsopropylquinolineHCID 178440986HCID 178440986, compound

Product 1

HCID 10494674HCID 10494674, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a cooled (ice bath) 2M diethyl ether solution of 4-tert-butylphenylmagnesium bromide (15 ml, 0.03 mol) was added dropwise under argon 15 ml of a tetrahydrofuran solution of 6-isopropylquinoline (5.13 g, 0.03 mol). The resulting mixture was refluxed for 5 hours, stirred at room temperature for 12 hours and quenched with water (80 ml). The yellow precipitate obtained was then filtered and washed with hexane. Crystallization in hexane:chloroform 40:1 yielded 3.7; of pure (±)-2-(4-tert-butylphenyl)-6-isopropylquinoline (40% yield). 1H NMR(CDCl3): 8.2 (m, ArH, 4H), 7.84 (m, ArH, 1H), 7.60 (m, ArH, 4H), 3.12 (s, CH(Me)2, 1H), 1.4 (s, CH(Me)2 and C(Me)3, 15H); Mass/Cl—NH3: MH31 304.

Workup

  1. temperatureThe resulting mixture was refluxed for 5 hours
  2. customquenched with water (80 ml)
  3. customThe yellow precipitate obtained
  4. filtrationwas then filtered
  5. washwashed with hexane
  6. customCrystallization in hexane:chloroform 40:1
  7. customyielded 3.7

Sources & evidence

ORD record
ord-3104e5582df748b99dcdfb2daa0ad12e
Source dataset
uspto-grants-2002_03
Patent number
US06358993B1

Reaction notes

Loading…