1,4-Dioxaspiro[4.5]decan-8-one → HCID 59556040, compound

HRID 1016009Notes

Reaction equation

HRID 1016009 reaction equation
Br[C:2]1[N:7]=[CH:6][C:5]([C:8]([OH:11])([CH3:10])[CH3:9])=[CH:4][CH:3]=1.C([Li])CCC.[CH2:17]1[O:27][C:20]2([CH2:25][CH2:24][C:23](=[O:26])[CH2:22][CH2:21]2)[O:19][CH2:18]1>C1COCC1.CCOCC>[OH:11][C:8]([C:5]1[CH:4]=[CH:3][C:2]([C:23]2([OH:26])[CH2:24][CH2:25][C:20]3([O:27][CH2:17][CH2:18][O:19]3)[CH2:21][CH2:22]2)=[N:7][CH:6]=1)([CH3:10])[CH3:9]

Participants

6

Reactant 3

HCID 5674151,4-Dioxaspiro[4.5]decan-8-oneHCID 223919732-(6-Bromo-3-pyridyl)-2-propanolHCID 178418339Butyllithium

Product 1

HCID 59556040HCID 59556040, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

2-(6-Bromopyridin-3-yl)propan-2-ol (1.08 g, 5 mmol) was dissolved in 10 mL of THF and 50 mL of anhydrous ether. After the solution was cooled to −78° C., 4.20 ml n-butyllithium (2.5 M, 11 mmol) was slowly dropped through a syringe in 10 min. After being stirred at −78° C. for 30 minutes, 1,4-cyclohexanedione mono-ethylene ketal (0.80 g, 5 mmol) was added. The reaction mixture was warmed up to room temperature during two hours and then quenched by addition of 5 mL of water. The mixture was extracted twice using EtOAc. The combined extracts were dried and concentrated. After flash column using 40-70% EtOAc in hexane, 0.48 g of white crystals were obtained (42% yield), MS: 294.1 (M++1).

Workup

  1. temperatureThe reaction mixture was warmed up to room temperature during two hours
  2. customquenched by addition of 5 mL of water
  3. extractionThe mixture was extracted twice using EtOAc
  4. customThe combined extracts were dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ca34e68980a14b7cba28b71ef291e82f
Source dataset
uspto-grants-2011_07
Patent number
US07985730B2

Reaction notes

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