Iodine → 1,3-Dioxolane-2-propionaldehyde

HRID 1888625Notes

Reaction equation

HRID 1888625 reaction equation
Br[CH2:2][CH2:3][CH:4]1[O:8][CH2:7][CH2:6][O:5]1.[Mg].II.CN([CH:15]=[O:16])C>C1COCC1>[O:5]1[CH2:6][CH2:7][O:8][CH:4]1[CH2:3][CH2:2][CH:15]=[O:16]

Participants

6

Reactant 4

HCID 807IodineHCID 6228DimethylformamideHCID 877762-(2-Bromoethyl)-1,3-dioxolaneHCID 5462224Magnesium

Product 1

HCID 36612141,3-Dioxolane-2-propionaldehydeYield 28%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To the solution of 2-(2-bromoethyl)-1,3-dioxolane (10 g, 55.2 mmol) in THF (50 mL) was added magnesium (1.6 g, 66.3 mmol) and trace amount of I2 as initiator. The reaction mixture was stirred at rt for 2 hrs. After cooling to −78° C., the mixture was quenched with dry DMF (1.39 g, 66.3 mmol) and kept at −78° C. for 2 hrs. After dilution with H2O the reaction mixture was extracted with CH2Cl2 (2×), followed by distillation (45-55° C. @ 8 mmHg) to afford 2 g (28%) of the title compound. MS (DCI/NH4+) m/z 131 (M+H)+.

Workup

  1. temperatureAfter cooling to −78° C.
  2. waitkept at −78° C. for 2 hrs
  3. extractionAfter dilution with H2O the reaction mixture was extracted with CH2Cl2 (2×)
  4. distillationfollowed by distillation (45-55° C. @ 8 mmHg)

Sources & evidence

ORD record
ord-269b90e54c5242bab823ce2f7bd50110
Source dataset
uspto-grants-2013_08
Patent number
US08501794B2

Reaction notes

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