Trimethyl orthoformate → HCID 15760462, compound

HRID 1901776Notes

Reaction equation

HRID 1901776 reaction equation
[CH:1](OC)([O:4][CH3:5])[O:2][CH3:3].O.[O-2].[O-2].[O-2].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O.[Al+3].[Al+3].C([C:28]1[S:32][C:31]([C:33]2[S:34][CH:35]=[CH:36][CH:37]=2)=[CH:30][CH:29]=1)=O>CCCCCC>[CH3:3][O:2][CH:1]([O:4][CH3:5])[C:28]1[S:32][C:31]([C:33]2[S:34][CH:35]=[CH:36][CH:37]=2)=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 9005Trimethyl orthoformateHCID 364428[2,2'-Bithiophene]-5-carboxaldehydeHCID 71586775Bentonite

Product 1

HCID 15760462HCID 15760462, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

Trimethyl orthoformate (7.5 ml) and montmorillonite K-10 (5.0 g) (Aldrich Chem. Co., Milwaukee, Wis.) were mixed and stirred at room temperature for 10 minutes. A solution of 5-formyl-2,2'-bithiophene (5.0 g) (Aldrich Chem. Co., Milwaukee, Wis.) in n-hexane (10 ml) was added and was stirred at room temperature. The reaction was monitored with thin layer chromatography until the reaction was completed. Montmorillonite K-10 was filtered. The filtrate was added to a saturated sodium bicarbonate aqueous solution and extracted with ethyl, acetate (15 ml×3). The extract was washed with brine, dried over anhydrous magnesium sulfate and concentrated to give light yellowish oily product (6.4 g).

Workup

  1. stirringwas stirred at room temperature
  2. filtrationMontmorillonite K-10 was filtered
  3. additionThe filtrate was added to a saturated sodium bicarbonate aqueous solution
  4. extractionextracted with ethyl, acetate (15 ml×3)
  5. washThe extract was washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-190fa998c3f2444eae9eb8fd7f366cbb
Source dataset
uspto-grants-1996_11
Patent number
US05578636

Reaction notes

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