4-Bromopyridine → 8-(4-Pyridinyl)-1,4-dioxaspiro[4.5]decan-8-ol

HRID 231215Notes

Reaction equation

HRID 231215 reaction equation
C([Li])CCC.Br[C:7]1[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=1.[CH2:13]1[O:23][C:16]2([CH2:21][CH2:20][C:19](=[O:22])[CH2:18][CH2:17]2)[O:15][CH2:14]1.[Cl-].[NH4+]>CCCCCC.CCOCC.O1CCCC1>[CH2:14]1[O:15][C:16]2([CH2:21][CH2:20][C:19]([OH:22])([C:7]3[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=3)[CH2:18][CH2:17]2)[O:23][CH2:13]1

Participants

8

Reactant 4

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

Product 1

HCID 137720538-(4-Pyridinyl)-1,4-dioxaspiro[4.5]decan-8-olYield 67.2%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

Thirty-five ml of ether was cooled to -78° C., to which 20 ml of a 1.6 mol n-butyl lithium solution in hexane was added. Next, 5 g of 4-bromopyridine was dissolved in 30 ml of ether and the solution was added to the mixture. Then, a solution of 5 g of 1,4-cyclohexanedione monoethyleneacetal in 30 ml of tetrahydrofuran was added to the mixture. After completion of the reaction, the reaction solution was poured into saturated ammonium chloride aqueous solution. The mixture was extracted with chloroform and the extract was purified to give 5 g of 4-hydroxy-4-(4-pyridyl)cyclohexanone ethyleneacetal.

Workup

  1. additionwas added
  2. additionthe solution was added to the mixture
  3. customAfter completion of the reaction
  4. extractionThe mixture was extracted with chloroform
  5. customthe extract was purified

Sources & evidence

ORD record
ord-424fabbef7374f15a0447ba7747e7663
Source dataset
uspto-grants-1989_07
Patent number
US04845228

Reaction notes

Loading…