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

HRID 850592Notes

Reaction equation

HRID 850592 reaction equation
CON(C)[C:4](=[O:13])[CH2:5][CH2:6][C:7]1([CH3:12])[O:11][CH2:10][CH2:9][O:8]1.CC(C[AlH]CC(C)C)C.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+].CCOCC>C1COCC1>[CH3:12][C:7]1([CH2:6][CH2:5][CH:4]=[O:13])[O:11][CH2:10][CH2:9][O:8]1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 9357Potassium Sodium TartrateHCID 14487Diisobutylaluminum hydrideHCID 15521920HCID 15521920, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-2 (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 were 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 2-3 as a colorless oil. TLC Rf =0.80 (silica, ethyl acetate). 1H NMR (300 MHz, CDCl3) δ 9.73 (s, 1H), 3.50 (d, 1H, J=16 Hz), 2.61 (d, 1H, J=21 Hz), 2.48 (m, 1H), 2.07 (t, 1H, J=7H), 1.33 (s, 3H).

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-45c3d10af3fc41b997675499146941bd
Source dataset
uspto-grants-2000_01
Patent number
US06017926

Reaction notes

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