Water → HCID 10382295, compound

HRID 1110353Notes

Reaction equation

HRID 1110353 reaction equation
C([Li])CCC.Br[C:7]1[N:12]=[C:11]2[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:10]2=[CH:9][C:8]=1[CH3:18].[CH:19]1[C:24]([CH:25]=[O:26])=[CH:23][CH:22]=[C:21]([C:27]([F:30])([F:29])[F:28])[CH:20]=1.O>CCCCCC.C1(C)C=CC=CC=1>[F:28][C:27]([F:29])([F:30])[C:21]1[CH:20]=[CH:19][C:24]([CH:25]([C:7]2[N:12]=[C:11]3[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:10]3=[CH:9][C:8]=2[CH3:18])[OH:26])=[CH:23][CH:22]=1

Participants

7

Reactant 4

HCID 962WaterHCID 679964-(Trifluoromethyl)benzaldehydeHCID 10399369HCID 10399369, compoundHCID 178418339Butyllithium

Product 1

HCID 10382295HCID 10382295, compoundYield 60.3%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent3×HCID 8058HexaneSolvent

Procedure

To a solution of 1.6M n-butyl lithium in n-hexane (16.5 ml) in toluene (20 ml) at -20° C., under nitrogen, was added a solution of 2-bromo-6,7,8,9-tetrahydro-3-methyl-5H-cyclohepta[b]pyridine (6.0 g, 0.025 m) in toluene (30 ml). The reaction mixture was kept at -20° C. for 0.25 hours and then blown over into a solution of a,a,a-tri-fluoro-p-tolualdehyde (4.7 g) in toluene (30 ml) at -20° C. The solution was allowed to warm up to room temperature and water added. The organic phase was separated with 2N hydrochloric acid. This was basified with solid potassium carbonate and extracted with chloroform. The combined chloroform extracts were dried (MgSO4) and evaporated. The residue was recrystallised from n-hexane to give the title compound, (5.05 g) m.p. 131°-3° C.

Workup

  1. customThe organic phase was separated with 2N hydrochloric acid
  2. extractionextracted with chloroform
  3. dry with materialThe combined chloroform extracts were dried (MgSO4)
  4. customevaporated
  5. customThe residue was recrystallised from n-hexane

Sources & evidence

ORD record
ord-9d420496c80547cc80f8bce04b3f7a2c
Source dataset
uspto-grants-1990_12
Patent number
US04975431

Reaction notes

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