Methanol → HCID 86748392, compound

HRID 1756617Notes

Reaction equation

HRID 1756617 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]([O:20][CH3:21])[C:8]([CH3:22])=[C:7]2[C:3]=1[C:4](=[O:23])[O:5][CH2:6]2.[CH3:24]O>O.C1(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][CH3:24])=[O:17])=[C:9]([O: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 2

HCID 887MethanolHCID 9948928HCID 9948928, compound

Product 1

HCID 86748392HCID 86748392, compoundYield 95.4%

Reagents, catalysts & solvents 1

HCID 521998p-Toluenesulfonic acid monohydrateCatalyst

Procedure

To a solution of 2.5 g (7.8 mmol) of (E)-6-(1,3-dihydro-4-amino-6-methoxy-7-methyl-3-oxoisobenzofuran-5-yl)-4-methyl-4-hexenoic acid in 50 ml (1.234 mol) of methanol was added 0.125 g (0.66 mmol) of p-toluene sulfonic acid monohydrate. The solution was stirred at room temperature for 2 days and then concentrated to a small volume. The residue was partitioned between water and ethyl acetate. The organic layer was dried over magnesium sulfate and concentrated to a solid. Recrystallization of this solid from hexane-ethyl acetate gave 2.48 g of methyl (E)-6-(1,3-dihydro-4-amino-6-methoxy-7-methyl-3-oxoisobenzofuran-5-yl)-4-methyl-4-hexenoate, mp 91°-93° C.

Workup

  1. concentrationconcentrated to a small volume
  2. customThe residue was partitioned between water and ethyl acetate
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. concentrationconcentrated to a solid
  5. customRecrystallization of this solid from hexane-ethyl acetate

Sources & evidence

ORD record
ord-3079a55c304142c0a29102bf23b77c4c
Source dataset
uspto-grants-1995_08
Patent number
US05441953

Reaction notes

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