Water → HCID 10424723, compound

HRID 1110352Notes

Reaction equation

HRID 1110352 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-5affdc48d5b64962a8e99bf8d160ca23
Source dataset
uspto-grants-1990_12
Patent number
US04975431

Reaction notes

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