Beta-Propiolactone → 1-(2-Hydroxyethyl)cyclopentan-1-ol

HRID 452985Notes

Reaction equation

HRID 452985 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5]Br.[Mg].[O:8]1[CH2:11][CH2:10][C:9]1=[O:12]>C1COCC1.II>[OH:8][CH2:11][CH2:10][C:9]1([OH:12])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 2365Beta-PropiolactoneHCID 80561,4-DibromobutaneHCID 5462224Magnesium

Product 1

HCID 141019991-(2-Hydroxyethyl)cyclopentan-1-olYield 18.2%

Reagents, catalysts & solvents 2

HCID 807IodineCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

1,4-dibromobutane (10 g, 46.3 mmol) in THF (100 mL) was treated with magnesium (2.81 g, 116 mmol) and I2 (100 mg) as initiator. The mixture was stirred at room temperature for 3 hours. To the mixture was added dropwise oxetan-2-one (3.34 g, 46.3 mmol) in THF (25 mL). The reaction was stirred at room temperature for 12 hours, quenched with saturated NH4Cl, and the mixture was extracted with isopropanol/CH2Cl2 (1:3) (2×100 mL). The organic layers were combined and dried over MgSO4, filtered and concentrated. The residue was purified by distillation at 95-100° C. (0.6 torr) to provide the title compound (1.1 g, 18%) MS (DCI/NH3) m/z 148 (M+NH4)+.

Workup

  1. stirringThe reaction was stirred at room temperature for 12 hours
  2. customquenched with saturated NH4Cl
  3. extractionthe mixture was extracted with isopropanol/CH2Cl2 (1:3) (2×100 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. distillationThe residue was purified by distillation at 95-100° C. (0.6 torr)

Sources & evidence

ORD record
ord-e14c468a4a5949c8b9e88fc8eea18ff9
Source dataset
uspto-grants-2013_07
Patent number
US08492371B2

Reaction notes

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