Iodine → 1,3-Dioxolane-2-propionaldehyde

HRID 253615Notes

Reaction equation

HRID 253615 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-aa73bea020b2489688a3f532ebf0dbbc
Source dataset
uspto-grants-2011_01
Patent number
US07872033B2

Reaction notes

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