Water → HCID 10424723, compound

HRID 1195721Notes

Reaction equation

HRID 1195721 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].[CH3:19][O:20][C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][CH:28]=1)[CH:24]=[O:25].O>CCCCCC.C1(C)C=CC=CC=1>[CH3:18][C:8]1[CH:9]=[C:10]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][C:11]2=[N:12][C:7]=1[CH:24]([C:23]1[CH:26]=[CH:27][CH:28]=[C:21]([O:20][CH3:19])[CH:22]=1)[OH:25]

Participants

7

Reactant 4

HCID 962WaterHCID 115693-MethoxybenzaldehydeHCID 10399369HCID 10399369, compoundHCID 178418339Butyllithium

Product 1

HCID 10424723HCID 10424723, compoundYield 59.5%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent3×HCID 8058HexaneSolvent

Procedure

To a solution of 1.6M n-butyl lithium in n-hexane (16.5 m,) in toluene (20 ml) at -20°, under nitrogen, was added a solution of 2-bromo-6,7,8,9-tetrahydro-3-methyl-5H-cyclohepta[b]pyridine (6 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 cooled solution (-20° C.) of 3-methoxybenzaldehyde (3.7 g) in toluene (30 ml) and allowed to warm up to room temperature. Water was added and the organic phase separated and treated with 2N hydrochloric acid. A precipitate formed and this was collected by filtration and treated with sodium carbonate solution, then chloroform. The organic phase was washed with water, dried (MgO4) and evaporated. Trituration with diethyl ether gave 1-(6,7,8,9-tetrahydro-3-methyl-5H-cyclohepta[b]pyrid-2-yl)-1-(3-methoxyphenyl)methanol (4.42 g, 59%) m.p. 104°-6° C.

Workup

  1. customthe organic phase separated
  2. additiontreated with 2N hydrochloric acid
  3. customA precipitate formed
  4. filtrationthis was collected by filtration
  5. additiontreated with sodium carbonate solution
  6. washThe organic phase was washed with water
  7. customdried (MgO4)
  8. customevaporated

Sources & evidence

ORD record
ord-9f0e5322706e4793b2e8adf9a8804006
Source dataset
uspto-grants-1992_05
Patent number
US05112832

Reaction notes

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