Tetrahydrofuran → 2-(6-Cyclohexyl-3-hydroxy-4-hexinyl)pyridine

HRID 2379022Notes

Reaction equation

HRID 2379022 reaction equation
C([Li])CCC.Br[C:7](Br)=[CH:8][CH2:9][CH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1.[N:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH:23]([CH3:26])C=O.C1C[O:30][CH2:29]C1>CCCCCC>[CH:10]1([CH2:9][C:8]#[C:7][CH:29]([OH:30])[CH2:26][CH2:23][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][N:17]=2)[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 110658841,1-Dibromo-3-cyclohexyl-1-propeneHCID 111263082-(Pyridin-2-YL)propanalHCID 178418339Butyllithium

Product 1

HCID 1317187582-(6-Cyclohexyl-3-hydroxy-4-hexinyl)pyridine

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

2 equivalents of a solution of n-butyllithium in hexane (1.4 M) are added at -78° C. to a solution of 0.1 mol of 1,1-dibromo-3-cyclohexyl-1-propene in THF. After warming to room temperature, the mixture is stirred for a further hour, then cooled to -78° C. and a solution of 0.]mol of 2-(2-pyridyl)propionaldehyde (prepared according to J. Pract. Chem. 19, 226 (1963)) is added. After warming to room temperature again, the mixture is poured onto ice and extracted with MTB. After drying, concentrating and chromatography on silica gel (EE/cyclohexane (1:1)) 20.4 g of the title compound are obtained as an oil.

Workup

  1. temperaturecooled to -78° C.
  2. temperatureAfter warming to room temperature again
  3. additionthe mixture is poured onto ice
  4. extractionextracted with MTB
  5. customAfter drying
  6. concentrationconcentrating

Sources & evidence

ORD record
ord-6334e2088dc740eb9c1b22057db2f62e
Source dataset
uspto-grants-1994_11
Patent number
US05360791

Reaction notes

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