Hexane → HCID 57803252, compound

HRID 1748500Notes

Reaction equation

HRID 1748500 reaction equation
CCCCCC.C([Li])CCC.Br[C:13]1[CH:18]=[CH:17][C:16]([Br:19])=[CH:15][N:14]=1.[CH2:20]1[O:30][C:23]2([CH2:28][CH2:27][C:26](=[O:29])[CH2:25][CH2:24]2)[O:22][CH2:21]1>C1(C)C=CC=CC=1.ClCCl>[Br:19][C:16]1[CH:17]=[CH:18][C:13]([C:26]2([OH:29])[CH2:27][CH2:28][C:23]3([O:30][CH2:20][CH2:21][O:22]3)[CH2:24][CH2:25]2)=[N:14][CH:15]=1

Participants

7

Reactant 4

HCID 8058HexaneHCID 693532,5-DibromopyridineHCID 5674151,4-Dioxaspiro[4.5]decan-8-oneHCID 178418339Butyllithium

Product 1

HCID 57803252HCID 57803252, compoundYield 53.7%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

1.6M n-Hexane solution of n-butyl lithium (66 ml) was added dropwise to a solution of 2,5-dibromopyridine (23.9 g) in toluene (420 ml) at −78° C., and stirred at the same temperature for an hour. Next, a solution of 1,4-cyclohexanedione monoethyleneketal (15 g) in dichloromethane (60 ml) was added dropwise, and the reaction solution was warmed up to room temperature over 7 hours. After completion of the reaction, a saturated aqueous solution of ammonium chloride and extracted with ethyl acetate three times. The organic solution was dried over anhydrous sodium sulfate and concentrated. The resulting residue was purified with silica gel column chromatography (n-hexane/ethyl acetate) and recrystallized from n-hexane/diethyl ether to give 8-(5-bromopyridin-2-yl)-1,4-dioxaspiro[4,5]decan-8-ol (16.2 g) as a white solid.

Workup

  1. customAfter completion of the reaction
  2. extractiona saturated aqueous solution of ammonium chloride and extracted with ethyl acetate three times
  3. dry with materialThe organic solution was dried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe resulting residue was purified with silica gel column chromatography (n-hexane/ethyl acetate)
  6. customrecrystallized from n-hexane/diethyl ether

Sources & evidence

ORD record
ord-7f16e2a4b5fe4d0fbcd31f3ca0908d09
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

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