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

HRID 717260Notes

Reaction equation

HRID 717260 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 rt for 3 h. To the mixture was added dropwise oxetan-2-one (3.34 g, 46.3 mmol) in THF (25 mL). The reaction was stirred at rt for 12 h, 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° [email protected] 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 rt for 12 h
  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.

Sources & evidence

ORD record
ord-df0f65b3741f412a8513234374eb6c26
Source dataset
uspto-grants-2015_11
Patent number
US09193713B2

Reaction notes

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