Cyclobutanone → 1633013-47-4

HRID 712681Notes

Reaction equation

HRID 712681 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Br:8])[CH:7]=1.[C:9]1(=[O:13])[CH2:12][CH2:11][CH2:10]1>C1COCC1>[Br:8][C:6]1[CH:7]=[C:2]([C:9]2([OH:13])[CH2:12][CH2:11][CH2:10]2)[CH:3]=[N:4][CH:5]=1

Participants

4

Reactant 2

HCID 14496CyclobutanoneHCID 693693,5-Dibromopyridine

Product 1

HCID 1176674521633013-47-4Yield 56.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-10 °C

Procedure

To a cooled (−20° C.) solution of 3,5-dibromopyridine (592 mg, 2.5 mmol) in THF (2 mL) is added a solution of isopropylmagnesium chloride-lithium chloride complex in THF (1.7 M, 1.4 mL, 2.4 mmol). The resultant mixture is stirred warming to −10° C. for 30 min. The mixture is recooled to −20° C. and cyclobutanone (230 μL, 3.0 mmol) is added. After stirring for 1 h, the reaction is quenched with saturated aqueous ammonium chloride solution and is extracted with EtOAc. The combined organic extracts are washed with water and brine, dried (MgSO4) and concentrated under reduced pressure. Purification by silica gel column chromatography (0-10% MeOH in DCM) provided 1-(5-bromo-pyridin-3-yl)-cyclobutanol (322 mg).

Workup

  1. customis recooled to −20° C.
  2. customthe reaction is quenched with saturated aqueous ammonium chloride solution
  3. extractionis extracted with EtOAc
  4. washThe combined organic extracts are washed with water and brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated under reduced pressure
  7. customPurification by silica gel column chromatography (0-10% MeOH in DCM)

Sources & evidence

ORD record
ord-52a22634602841c2a1f6db7c8875e53e
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

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