Iodine → 1,3-Dioxolane-2-propionaldehyde

HRID 76253

Reaction equation

HRID 76253 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-cb2e95cbfab14f60ac1af2e9fbf5e1e1
Source dataset
uspto-grants-2014_09
Patent number
US08835475B2

Linked notes

Loading…