Acetaldehyde → HCID 57457555, compound

HRID 2111840Notes

Reaction equation

HRID 2111840 reaction equation
C([N-]C(C)C)(C)C.[Li+].[C:9]1([C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:12][O:11]1)=[O:10].[CH:19](=[O:21])[CH3:20]>O1CCCC1>[OH:21][CH:19]([CH:12]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:18]=2[C:9](=[O:10])[O:11]1)[CH3:20]

Participants

5

Reactant 3

HCID 177AcetaldehydeHCID 6885PhthalideHCID 2724682Lithium diisopropylamide

Product 1

HCID 57457555HCID 57457555, compoundYield 49.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

A dry tetrahydrofuran solution (100 mL) of lithium diisopropyl amide (26.9 mmol) was cooled to −78 degree in a current of nitrogen, and a tetrahydrofuran solution (100 mL) of phthalide (3.0 g, 22.4 mmol) was dripped in. After stirring at −78° C. for 30 minutes, acetaldehyde (1.19 g, 26.9 mmol) was slowly added and stirred at −50° C. for 4 hours. After the temperature had risen to room temperature, distilled water was added and the mixture extracted with ethyl acetate. The organic phase was washed with distilled water and saturated brine, and dried with anhydrous sodium sulfate. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/6), and the target compound (1.96 g, 49%) was obtained as a yellow oily residue.

Workup

  1. stirringstirred at −50° C. for 4 hours
  2. customhad risen to room temperature
  3. distillationdistilled water
  4. additionwas added
  5. extractionthe mixture extracted with ethyl acetate
  6. washThe organic phase was washed with distilled water and saturated brine
  7. dry with materialdried with anhydrous sodium sulfate
  8. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/6)

Sources & evidence

ORD record
ord-239f9fd84ea74c7e88ed79b1e6a42e76
Source dataset
uspto-grants-2009_04
Patent number
US07521455B2

Reaction notes

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