Water → HCID 10333512, compound

HRID 1494542Notes

Reaction equation

HRID 1494542 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].[S:19]1[CH:23]=[CH:22][CH:21]=[C:20]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:20]1[S:19][CH:23]=[CH:22][CH:21]=1)[OH:25]

Participants

7

Reactant 4

HCID 962WaterHCID 73642-ThiophenecarboxaldehydeHCID 10399369HCID 10399369, compoundHCID 178418339Butyllithium

Product 1

HCID 10333512HCID 10333512, compoundYield 64.7%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 8058HexaneSolvent

Procedure

To a solution of 1.6M n-butyl lithium in n-hexane (16.5 ml) in toluene (20 ml) at -70° C., 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) and the mixture kept at -20° C. for 0.25 hours. This was blown over into a solution of 2-thiophenecarboxaldehyde (3.0 g) in toluene (30 ml) kept at -20° C., then allowed to warm to room temperature and water added. The organic phase was extracted with 2N hydrochloric acid, then 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 (4.42 g), m.p. 102°-4° C.

Workup

  1. customkept at -20° C.
  2. extractionThe organic phase was extracted with 2N hydrochloric acid
  3. extractionextracted with chloroform
  4. dry with materialThe combined chloroform extracts were dried (MgSO4)
  5. customevaporated
  6. customThe residue was recrystallised from n-hexane

Sources & evidence

ORD record
ord-9317c0b242a64401b0268a1d7e205cbf
Source dataset
uspto-grants-1991_06
Patent number
US05026854

Reaction notes

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