Hydrochloric Acid → Methyl 4-[7-(3-carboxy-2,3,4,5-tetrahydro-5-oxofuran-2-yl)naphth-1-ylmethyl]-3-methoxybenzoate

HRID 2371805Notes

Reaction equation

HRID 2371805 reaction equation
C(N(CC)CC)C.[CH:8]([C:10]1[CH:19]=[C:18]2[C:13]([CH:14]=[CH:15][CH:16]=[C:17]2[CH2:20][C:21]2[CH:30]=[CH:29][C:24]([C:25]([O:27][CH3:28])=[O:26])=[CH:23][C:22]=2[O:31][CH3:32])=[CH:12][CH:11]=1)=[O:9].[C:33]1(=[O:39])[O:38][C:36](=[O:37])[CH2:35][CH2:34]1.Cl>[Cl-].[Zn+2].[Cl-].C(OCC)(=O)C.C(Cl)Cl>[C:36]([CH:35]1[CH2:34][C:33](=[O:39])[O:9][CH:8]1[C:10]1[CH:19]=[C:18]2[C:13]([CH:14]=[CH:15][CH:16]=[C:17]2[CH2:20][C:21]2[CH:30]=[CH:29][C:24]([C:25]([O:27][CH3:28])=[O:26])=[CH:23][C:22]=2[O:31][CH3:32])=[CH:12][CH:11]=1)([OH:38])=[O:37]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 7922Succinic anhydrideHCID 8471TriethylamineHCID 19906378Methyl 4-[7-formylnaphth-1-ylmethyl]-3-methoxybenzoate

Product 1

HCID 19906368Methyl 4-[7-(3-carboxy-2,3,4,5-tetrahydro-5-oxofuran-2-yl)naphth-1-ylmethyl]-3-methoxybenzoate

Reagents, catalysts & solvents 3

HCID 3007855ZincchlorideCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Triethylamine (4.54 g) was added to a mixture of methyl 4-[7-formylnaphth-1-ylmethyl]-3-methoxybenzoate (5.00 g), succinic anhydride (2.99 g), zinc chloride (6.11 g) and methylene chloride (50 ml). During the addition, the reaction was cooled with an ambient temperature bath. The mixture was stirred for 18 h and poured into a vigorously stirred solution of 1:1 ethyl acetate:2N hydrochloric acid (500 ml). The organic layer was washed (water, brine) and dried (MgSO4). After the evaporation of solvent and dissolving the residue in saturated sodium bicarbonate, the solution was washed with ether. The aqueous solution was neutralized with 6N hydrochloric acid, acidified to pH 2 with 1N hydrochloric acid and extracted with ethyl acetate. The organic layer was washed (water, brine), dried (MgSO4) and evaporated to give methyl 4-[7-(3-carboxy-2,3,4,5-tetrahydro-5-oxofuran-2-yl)naphth-1-ylmethyl]-3-methoxybenzoate (6.16 g, 95%, as a mixture of diastereomers) as a pale yellow foam; MS(CI), m/e=434(M+H).

Workup

  1. additionDuring the addition
  2. washThe organic layer was washed (water, brine)
  3. dry with materialdried (MgSO4)
  4. customAfter the evaporation of solvent
  5. dissolutiondissolving the residue in saturated sodium bicarbonate
  6. washthe solution was washed with ether
  7. extractionextracted with ethyl acetate
  8. washThe organic layer was washed (water, brine)
  9. dry with materialdried (MgSO4)
  10. customevaporated

Sources & evidence

ORD record
ord-74368654352e4dee81b3fd3e8d45b713
Source dataset
uspto-grants-1992_03
Patent number
US05095038

Reaction notes

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