Trimethyl orthoformate → HCID 14130325, compound

HRID 1708981Notes

Reaction equation

HRID 1708981 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:14][CH2:15][C:16]#[CH:17])[C:9]=1[O:10][CH2:11][C:12]#[CH:13])C=O.[CH:18]([O:23][CH3:24])([O:21][CH3:22])OC.[Cl-].[NH4+]>CO>[CH3:24][O:23][CH:18]([O:21][CH3:22])[C:4]1[CH:7]=[C:8]([O:14][CH2:15][C:16]#[CH:17])[C:9]([O:10][CH2:11][C:12]#[CH:13])=[C:2]([Cl:1])[CH:3]=1

Participants

5

Reactant 3

HCID 9005Trimethyl orthoformateHCID 25517Ammonium ChlorideHCID 141303053-Chloro-4,5-dipropargyloxybenzaldehyde

Product 1

HCID 14130325HCID 14130325, compoundYield 79.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 3-chloro-4,5-dipropargyloxybenzaldehyde (1.0 g), trimethyl orthoformate (4.0 g) and ammonium chloride (0.05 g) in methanol (20 ml) was stirred under reflux for 3 hours, and the resultant solution was poured into ice-water and extracted with ethyl acetate. The extract was washed with water, dried over magnesium sulfate and concentrated under reduced pressure. The residue was subjected to alumina chromatography using toluene as an eluent to give 3-chloro-4,5-dipropargyloxybenzaldehyde dimetylacetal (0.94 g). nD21.0 1.5344.

Workup

  1. temperatureunder reflux for 3 hours
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-09eb7b8da44d4ffa849882e2e9944187
Source dataset
uspto-grants-1990_08
Patent number
US04946865

Reaction notes

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