Dimethylformamide → Methyl 8-methoxy-1,2,3,4-tetrahydronaphthalene-2-carboxylate

HRID 1243144Notes

Reaction equation

HRID 1243144 reaction equation
[CH3:1]N(C=O)C.[CH3:6][O:7][C:8]1[CH:9]=[CH:10][CH:11]=[C:12]2[C:17]=1[CH2:16][CH:15]([C:18]([OH:20])=[O:19])[CH2:14][CH2:13]2.CI.C([O-])([O-])=O.[K+].[K+]>C(OCC)(=O)C>[CH3:1][O:19][C:18]([CH:15]1[CH2:14][CH2:13][C:12]2[C:17](=[C:8]([O:7][CH3:6])[CH:9]=[CH:10][CH:11]=2)[CH2:16]1)=[O:20]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 36247098-methoxy-1,2,3,4-tetrahydronaphthalene-2-carboxylic Acid

Product 1

HCID 13058286Methyl 8-methoxy-1,2,3,4-tetrahydronaphthalene-2-carboxylate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a DMF solution (30 mL) of 8-methoxy-1,2,3,4-tetrahydro-naphthalene-2-carboxylic acid (5.0 g, 24 mmol) was added MeI (7.1 g, 50 mmol) and K2CO3 (6.9 g, 50 mmol). The mixture was allowed to stir overnight and ethyl acetate (200 mL) was added. The resulting solution was washed with water (3×50 mL) and brine (50 mL) to provide 8-methoxy-1,2,3,4-tetrahydro-naphthalene-2-carboxylic acid methyl ester (6.6 g).

Workup

  1. washThe resulting solution was washed with water (3×50 mL) and brine (50 mL)

Sources & evidence

ORD record
ord-3ff1f3a69cb44de592296d9aced13302
Source dataset
uspto-grants-2006_10
Patent number
US07115767B2

Reaction notes

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