Sodium Methoxide → HCID 68740990, compound

HRID 1445330Notes

Reaction equation

HRID 1445330 reaction equation
C([O:4][CH2:5][CH:6]1[CH:11]([O:12]C(=O)C)[CH:10]([O:16]C(=O)C)[CH:9]([O:20]C(=O)C)[CH:8]([O:24][C:25]2[CH:29]=[CH:28][S:27][C:26]=2[CH:30]=[CH:31][C:32]2[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][CH:33]=2)[O:7]1)(=O)C.C[O-].[Na+]>CO>[OH:4][CH2:5][CH:6]1[CH:11]([OH:12])[CH:10]([OH:16])[CH:9]([OH:20])[CH:8]([O:24][C:25]2[CH:29]=[CH:28][S:27][C:26]=2[CH:30]=[CH:31][C:32]2[CH:33]=[CH:34][C:35]([O:38][CH3:39])=[CH:36][CH:37]=2)[O:7]1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 68742418HCID 68742418, compound

Product 1

HCID 68740990HCID 68740990, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
22 °C

Procedure

150 mg of 3,4,5-triacetoxy-6-{2-[2-(4-methoxy-phenyl)-vinyl]-thiophen-3-yloxy}-tetrahydropyran-2-ylmethyl acetate were suspended in 10 ml of dry methanol. 1.0 ml of a methanolic NaOMe solution (10 mg/ml) was added. The solution was stirred at 22° C. for 18 h. Amberlyst 15 (H+ form) was added and the solution was diluted with 10 ml of MeOH and filtered, and the residue was washed with 20 ml of methanol. The organic phase was concentrated, and the residue was purified by chromatography on silica gel. 100 mg of the product with the molecular weight: 394.45 (C19H22O7S), MS (ESI): 417 (M+Na+); 412 (M+NH4+) were obtained.

Workup

  1. additionAmberlyst 15 (H+ form) was added
  2. filtrationfiltered
  3. washthe residue was washed with 20 ml of methanol
  4. concentrationThe organic phase was concentrated
  5. customthe residue was purified by chromatography on silica gel
  6. custom412 (M+NH4+) were obtained

Sources & evidence

ORD record
ord-54ac798e0c214deba800d866af44c86b
Source dataset
uspto-grants-2010_02
Patent number
US07666848B2

Reaction notes

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