Methanol → HCID 15161057, compound

HRID 1535053Notes

Reaction equation

HRID 1535053 reaction equation
[C:1]([C:5]1[C:6]([O:37][CH3:38])=[N:7][C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[C:10]([S:15][CH2:16][CH2:17][CH2:18][C:19]1[C:35]([OH:36])=[CH:34][C:22]3[CH2:23][CH:24]([CH2:26][CH2:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[O:25][C:21]=3[CH:20]=1)[CH:9]=2)([O:3]C)=[O:2].CO.[OH-].[Na+]>>[C:1]([C:5]1[C:6]([O:37][CH3:38])=[N:7][C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[C:10]([S:15][CH2:16][CH2:17][CH2:18][C:19]1[C:35]([OH:36])=[CH:34][C:22]3[CH2:23][CH:24]([CH2:26][CH2:27][C:28]4[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=4)[O:25][C:21]=3[CH:20]=1)[CH:9]=2)([OH:3])=[O:2]

Participants

4

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 15161056HCID 15161056, compound

Product 1

HCID 15161057HCID 15161057, compoundYield 21%

Conditions

Temperature
75 °C

Procedure

A mixture of 6-[3-(3-carbomethoxy-2-methoxyquinolin-7-yl)thiopropyl]-5-hydroxy-2-(2-phenylethyl)-2,3-dihydrobenzofuran, E26, (794 mg; 1.5 mmoles), methanol (12 mL) and 1N sodium hydroxide (12 mL) was heated in an oil bath at 75° C. and under nitrogen atmosphere for 45 minutes. The mixture was concentrated in vacuo to remove most of the methanol and the residue was neutralized with excess 25% ammonium acetate solution. The mixture was extracted with ethylacetate, dried (MgSO4), filtered and concentrated in vacuo. The residue was chromatographed on silica gel using 65:30:5 hexane:ethylacetate:acetic acid as eluent to yield 165 mgs (21%) of 6-[3-(3-carboxy-2-methoxyquinolin-7-yl)thiopropyl]-5-hydroxy-2-(2-phenylethyl)-2,3-dihydrobenzofuran, E27, m.p. 157°-161° C.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customto remove most of the methanol
  3. extractionThe mixture was extracted with ethylacetate
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was chromatographed on silica gel using 65:30:5 hexane

Sources & evidence

ORD record
ord-0dfed307cce64c7eb1f19a8f7d0f6d65
Source dataset
uspto-grants-1992_02
Patent number
US05091533

Reaction notes

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