Diethyl Ether → 1,3-Dioxolane-2-propanal, 2-methyl-

HRID 322080Notes

Reaction equation

HRID 322080 reaction equation
[CH3:1][CH:2](C[AlH]CC(C)C)C.[C@H:10](O)([C:16]([O-:18])=[O:17])[C@@H:11](O)[C:12]([O-:14])=O.[Na+].[K+].[CH3:22]COCC>C1COCC1>[CH3:22][C:16]1([CH2:10][CH2:11][CH:12]=[O:14])[O:18][CH2:2][CH2:1][O:17]1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 9357Potassium Sodium TartrateHCID 14487Diisobutylaluminum hydride

Product 1

HCID 5600401,3-Dioxolane-2-propanal, 2-methyl-

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-2 (44.74 g, 0.22 mol) in 400 mL THF at −78° C. was added DIBAL (264 mL 1 M in hexanes, 0.264 mol) over 10 minutes. After stirring for 1 h, 350 ml of 1.0 M Rochelle's salt and 300 ml ether was added followed by the removal of the cooling bath. After stirring for 1 h, the organic portion was separated and dried over Na2SO4. Evaporative removal of the solvent gave 4-3 as a colorless oil.

Workup

  1. customfollowed by the removal of the cooling bath
  2. stirringAfter stirring for 1 h
  3. customthe organic portion was separated
  4. dry with materialdried over Na2SO4
  5. customEvaporative removal of the solvent

Sources & evidence

ORD record
ord-e77ae65f997d47cbba2115e1f41757eb
Source dataset
uspto-grants-2001_04
Patent number
US06211191B1

Reaction notes

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