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

HRID 1931087Notes

Reaction equation

HRID 1931087 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 18.4%

Reagents, catalysts & solvents 2

HCID 807IodineCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1,4-dibromobutane (10 g, 46 mmol) in THF (100 mL) was treated with magnesium (2.81 g, 116 mmol) and I2 (100 mg). The mixture was stirred at room temperature for 3 hours a solution of oxetan-2-one (3.34 g, 46.3 mmol) in THF (25 mL) was added dropwise. The reaction mixture was stirred at room temperature for 12 hours then quenched with saturated aqueous NH4Cl and extracted with isopropanol/CH2Cl2 (1:3) (2×100 mL). The combined organic extracts were dried over MgSO4, filtered and concentrated. The residue was purified by distillation (95-100° C. at 0.6 Ton) to provide 1.1 g (18%) of the title compound. MS (DCI/NH3) m/z 148 (M+NH4)−.

Workup

  1. additionwas added dropwise
  2. customthen quenched with saturated aqueous NH4Cl
  3. extractionextracted with isopropanol/CH2Cl2 (1:3) (2×100 mL)
  4. dry with materialThe combined organic extracts were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. distillationThe residue was purified by distillation (95-100° C. at 0.6 Ton)

Sources & evidence

ORD record
ord-483ae7bc4f4d47308577c769c666b5d3
Source dataset
uspto-grants-2012_05
Patent number
US08188135B2

Reaction notes

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