2-Bromopyridine → HCID 21187637, compound

HRID 2225224Notes

Reaction equation

HRID 2225224 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.C([Li])CCC.[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>C(OCC)C>[N:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[C:19]1([OH:22])[CH2:20][CH2:21][C:16]2([O:23][CH2:13][CH2:14][O:15]2)[CH2:17][CH2:18]1

Participants

5

Reactant 3

HCID 79732-BromopyridineHCID 5674151,4-Dioxaspiro[4.5]decan-8-oneHCID 178418339Butyllithium

Product 1

HCID 21187637HCID 21187637, compoundYield 129.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
-70 °C

Procedure

2-Bromopyridine (1.40 g, 8.86 mmol, 1 eq) was dissolved in diethyl ether (30 mL) at room temperature under nitrogen then cooled to −70° C. Added 1.6M n-butyllithium (5.54 mL, 8.86 mmol, 1 eq) dropwise via an addition funnel. Stirred at −70° C. for 1 hour then added 1,4-cyclohexanedione-mono-ethylene ketal (1.52 g, 9.57 mmol, 1.1 eq) as a diethyl ether (30 mL) solution, dropwise via an addition funnel. Stirred at 0° C. for 1 hour. Quenched with saturated ammonium chloride (25 mL). Separated the 2 layers. The aqueous layer was extracted 2 times more with methylene chloride. The organic layers were combined, dried (sodium sulfate) and stripped to give an oil. Purified over silica gel in 9:1 to 1:1 hexanes/ethyl acetate to give 8-(2-pyridinyl)-1,4-dioxaspiro[4.5]decan-8-ol (2.70 g) of an amber oil. MS found: (M+H)+=236.1

Workup

  1. stirringStirred at 0° C. for 1 hour
  2. customQuenched with saturated ammonium chloride (25 mL)
  3. customSeparated the 2 layers
  4. extractionThe aqueous layer was extracted 2 times more with methylene chloride
  5. dry with materialdried (sodium sulfate)
  6. customto give an oil
  7. customPurified over silica gel in 9:1 to 1:1 hexanes/ethyl acetate

Sources & evidence

ORD record
ord-483eb5fb6dd74d56af9532cf61ba219f
Source dataset
uspto-grants-2008_05
Patent number
US07378409B2

Reaction notes

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