4-Bromopyridine → HCID 21243518, compound

HRID 621705Notes

Reaction equation

HRID 621705 reaction equation
C([Li])CCC.Br[C:7]1[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=1.C1O[C:16]2([CH2:21][CH2:20][C:19](=[O:22])[CH2:18][CH2:17]2)[O:15]C1.[Cl-].[NH4+]>CCCCCC.CCOCC.O1CCCC1>[OH:22][C:19]1([C:7]2[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=2)[CH2:20][CH2:21][C:16](=[O:15])[CH2:17][CH2:18]1

Participants

8

Reactant 4

HCID 142684-BromopyridineHCID 25517Ammonium ChlorideHCID 5674151,4-Dioxaspiro[4.5]decan-8-oneHCID 178418339Butyllithium

Product 1

HCID 21243518HCID 21243518, compoundYield 82.6%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

35 ml of ether was cooled to -78° C. and 20 ml of a 1.6 M solution of n-butyllithium in hexane was added thereto. To the obtained mixture, 5 g of 4-bromopyridine dissolved in 30 ml of ether was added. Then 5 g of 1,4-cyclohexanedione monoethylene acetal dissolved in 30 ml of tetrahydrofuran was further added thereto. After the completion of the reaction, the reaction mixture was poured into a saturated aqueous solution of ammonium chloride and purified by extracting with chloroform to give 5 g of 4-hydroxy-4-(4-pyridyl)cyclohexanone

Workup

  1. additionwas added
  2. additionwas further added
  3. customAfter the completion of the reaction
  4. custompurified
  5. extractionby extracting with chloroform

Sources & evidence

ORD record
ord-2cf68b5674c54e7a959836b16b919515
Source dataset
uspto-grants-1989_04
Patent number
US04824952

Reaction notes

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