Acetic Acid → HCID 73691528, compound

HRID 636747Notes

Reaction equation

HRID 636747 reaction equation
[F:1][C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:3]=1[CH:4]=O.[CH3:11][C:12]([N+:21]([O-])=[O:22])([CH3:20])[CH2:13][CH2:14][CH:15]1[O:19][CH2:18][CH2:17][O:16]1.C(O)(=O)C>C(O)C.[Zn]>[F:1][C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:3]=1[CH:4]=[N+:21]([C:12]([CH3:20])([CH3:11])[CH2:13][CH2:14][CH:15]1[O:16][CH2:17][CH2:18][O:19]1)[O-:22]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 737702,4-DifluorobenzaldehydeHCID 5525632-(3-Methyl-3-nitrobutyl)-1,3-dioxolane

Product 1

HCID 73691528HCID 73691528, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 702EthanolSolvent

Procedure

A suspension of 2,4-difluorobenzaldehyde (290.6 mg, 2.04 mmol), 2-(3-methyl-3-nitrobutyl)-1,3-dioxolane (776.8 mg, 4.11 mmol) and zinc (402.7 mg, 6.16 mmol) in ethanol (5 ml) was cooled to 0° C. in ice-water bath. Acetic acid (0.69 ml, 12.0 mmol) was added dropwise to the mixture. The mixture was gradually warmed to room temperature and stirred for 10 hours and let stand overnight. The mixture was filtered through Celite® bed and the filtrate was concentrated and purified by silica gel chromatography (hexane/ethyl acetate=4/1-1/1) to give the title compound (419.4 mg; 69%).

Workup

  1. waitlet stand overnight
  2. filtrationThe mixture was filtered through Celite® bed
  3. concentrationthe filtrate was concentrated
  4. custompurified by silica gel chromatography (hexane/ethyl acetate=4/1-1/1)

Sources & evidence

ORD record
ord-5124b57524b047ebb2da08459d684bd9
Source dataset
uspto-grants-2001_02
Patent number
US06194461B1

Reaction notes

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