Dimethylformamide → Methyl 5,6,7,8-tetrahydro-5-methoxy-2-naphthalenecarboxylate

HRID 1004444Notes

Reaction equation

[H-].[Na+].Cl.C1(C2C=CC=CC=2)C=CC=CC=1N[C:11]([C:13]1[CH:22]=[CH:21][C:20]2[C:19](=[O:23])[CH:18](CCN3CCC(C4C=CC=CC=4)CC3)[CH2:17][CH2:16][C:15]=2[CH:14]=1)=[O:12].[CH3:44]I.CN([CH:49]=[O:50])C>>[CH3:44][O:23][CH:19]1[CH2:18][CH2:17][CH2:16][C:15]2[CH:14]=[C:13]([C:11]([O:50][CH3:49])=[O:12])[CH:22]=[CH:21][C:20]1=2

Participants

Reactant 4

HCID 6228Dimethylformamide

HCID 6328Methyl iodide2×

HCID 24758Sodium hydride2×

HCID 131721763HCID 131721763, compound

Product 1

HCID 86755324Methyl 5,6,7,8-tetrahydro-5-methoxy-2-naphthalenecarboxylateYield 63%

Conditions

Temperature: 0 °C

Procedure

Sodium hydride (80% oil dispersion, 28 mg, 0.93 mmol) was added to a solution of 2 (0.19 g, 0.93 mmol) in DMF (2 mL) stirring at 0° C. Methyl iodide (0.13 g, 58 mL, 0.93 mmol) was added. After stirring at 0° C. for 2 hours and at ambient temperature for 30 minutes, additional sodium hydride (14 mg, 0.47 mmol) and methyl iodide (29 mL, 0.47 mmol) were added. After stirring an additional 3 hours, the reaction was quenched with 0.1N HCl and transferred to a separatory funnel with CH2Cl2. Extraction with CH2Cl2 (2×40 mL) and drying over MgSO4 afforded 0.33 g of crude product after evaporation of the solvent. Flash chromatography (silica, 25 mm dia, 10% EtOAc/hexane) afforded 0.13 g (63%) of the title compound.

Workup

stirringAfter stirring at 0° C. for 2 hours and at ambient temperature for 30 minutes
stirringAfter stirring an additional 3 hours
customthe reaction was quenched with 0.1N HCl
customtransferred to a separatory funnel with CH2Cl2
extractionExtraction with CH2Cl2 (2×40 mL)
dry with materialdrying over MgSO4
customafforded 0.33 g of crude product
customafter evaporation of the solvent

Sources & evidence

ORD record: ord-03d5251ba53a42ff90b0b8547cb4ba66
Source dataset: uspto-grants-2000_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06048877

Reaction notes

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