Methanol → 3-Methoxythiophene-2-carbaldehyde

HRID 2211581Notes

Reaction equation

HRID 2211581 reaction equation
OCC1C(O)C(O)C(O)[CH:5]([O:12][C:13]2[CH:17]=[CH:16][S:15][C:14]=2[CH:18]=CC2C=CC(OC)=CC=2)O1.C[OH:29]>[Pd]>[CH3:5][O:12][C:13]1[CH:17]=[CH:16][S:15][C:14]=1[CH:18]=[O:29]

Participants

4

Reactant 2

HCID 887MethanolHCID 68740990HCID 68740990, compound

Product 1

HCID 5883153-Methoxythiophene-2-carbaldehyde

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

50 mg of 2-hydroxymethyl-6-{2-[2-(4-methoxy-phenyl)-vinyl]-thiophen-3-yloxy}-tetrahydro-pyran-3,4,5-triol were dissolved in 10 ml of methanol. 20 mg of palladium on activated carbon were added and the solution was stirred under a hydrogen atmosphere for 18 h. The catalyst was filtered off and washed with 60 ml of methanol, and the organic phase was concentrated. The residue was chromatographed on silica gel (ethyl acetate). 18 mg of the product with the molecular weight of 396.46 (C19H24O7S); MS (ESI): 419.05 (M+Na+), 414.10 (M+NH4+).

Workup

  1. filtrationThe catalyst was filtered off
  2. washwashed with 60 ml of methanol
  3. concentrationthe organic phase was concentrated
  4. customThe residue was chromatographed on silica gel (ethyl acetate)

Sources & evidence

ORD record
ord-d32097b2eed44c7c83f9d0cf747306fb
Source dataset
uspto-grants-2006_09
Patent number
US07101856B2

Reaction notes

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