Methanol → HCID 86749564, compound

HRID 260118Notes

Reaction equation

HRID 260118 reaction equation
[NH2:1][C:2]1[C:10]([CH2:11]/[CH:12]=[C:13](\[CH3:19])/[CH2:14][CH2:15][C:16]([OH:18])=[O:17])=[C:9]([CH2:20][CH3:21])[C:8]([CH3:22])=[C:7]2[C:3]=1[C:4](=[O:23])[O:5][CH2:6]2.CO.O.[C:27]1(C)C=CC(S(O)(=O)=O)=CC=1>>[NH2:1][C:2]1[C:10]([CH2:11]/[CH:12]=[C:13](\[CH3:19])/[CH2:14][CH2:15][C:16]([O:18][CH3:27])=[O:17])=[C:9]([CH2:20][CH3:21])[C:8]([CH3:22])=[C:7]2[C:3]=1[C:4](=[O:23])[O:5][CH2:6]2

Participants

4

Reactant 3

HCID 887MethanolHCID 521998p-Toluenesulfonic acid monohydrateHCID 9797036HCID 9797036, compound

Product 1

HCID 86749564HCID 86749564, compound

Procedure

To a solution of 2.5 g of (E)-6-(4-amino-1,3-dihydro-6-ethyl-7-methyl-3-oxoisobenzofuran-5-yl)-4-methyl-4-hexenoic acid in 50 ml (1.234 mol) of methanol is added 0.125 g of p-toluenesulfonic acid monohydrate. The solution is stirred at room temperature for 2 days and then concentrated to a small volume, and the residue partitioned between water and ethyl acetate. The organic layer is dried over magnesium sulfate and concentrated to give methyl (E)-6-(4-amino-1,3-dihydro-6-ethyl-7-methyl-3-oxoisobenzofuran-5-yl)-4-methyl-4-hexenoate.

Workup

  1. concentrationconcentrated to a small volume
  2. customthe residue partitioned between water and ethyl acetate
  3. dry with materialThe organic layer is dried over magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-8e63dfbebe824598ad685e99e89832f7
Source dataset
uspto-grants-1996_06
Patent number
US05525602

Reaction notes

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