2-Thiophenecarboxaldehyde → 2-(Diethoxymethyl)thiophene

HRID 1604452Notes

Reaction equation

HRID 1604452 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1C=O.[CH:8]([O:15][CH2:16][CH3:17])([O:12][CH2:13][CH3:14])OCC.C([O-])([O-])=O.[K+].[K+]>C(O)C.Cl>[CH2:16]([O:15][CH:8]([O:12][CH2:13][CH3:14])[C:2]1[S:1][CH:5]=[CH:4][CH:3]=1)[CH3:17]

Participants

6

Reactant 3

HCID 73642-ThiophenecarboxaldehydeHCID 11430Potassium CarbonateHCID 31214Ethyl orthoformate

Product 1

HCID 122800182-(Diethoxymethyl)thiopheneYield 90%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 702EthanolSolvent

Procedure

A solution of 22.4 g (200 mmol) of 2-thiophene carboxaldehyde and 44.4 g (300 mmol) of triethyl orthoformate in ethanol (200 mL) with 3-5 drops of concentrated HCl was heated at reflux for 4 hrs. The reaction mixture was then neutralized with K2CO3. After filtered and concentrated, 33.5 g (90% yield) of 2-(diethoxymethyl)-thiophene was distilled under reduced pressure (bp 156° C./1 torr).

Workup

  1. temperatureat reflux for 4 hrs
  2. filtrationAfter filtered
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-5e613cdf8b414734a3a08d6d003e8790
Source dataset
uspto-grants-1999_11
Patent number
US05994394

Reaction notes

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