Methanol → Methyl 5-oxo-5,6,7,8-tetrahydronaphthalene-2-carboxylate

HRID 2402391Notes

Reaction equation

HRID 2402391 reaction equation
[O:1]=[C:2]1[CH2:11][CH2:10][CH2:9][C:8]2[CH:7]=[C:6]([C:12]([OH:14])=[O:13])[CH:5]=[CH:4][C:3]1=2.CO.[CH3:17][Si](C=[N+]=[N-])(C)C>C1COCC1>[O:1]=[C:2]1[CH2:11][CH2:10][CH2:9][C:8]2[CH:7]=[C:6]([C:12]([O:14][CH3:17])=[O:13])[CH:5]=[CH:4][C:3]1=2

Participants

5

Reactant 3

HCID 887MethanolHCID 167693TrimethylsilyldiazomethaneHCID 28184935-Oxo-5,6,7,8-tetrahydronaphthalene-2-carboxylic acid

Product 1

HCID 15309116Methyl 5-oxo-5,6,7,8-tetrahydronaphthalene-2-carboxylateYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-oxo-5,6,7,8-tetrahydronaphthalene-2-carboxylic acid (10.0 g, 52.6 mmol) in THF (52.6 mL) and MeOH (10.64 mL, 263 mmol) at rt was added trimethylsilyldiazomethane (2.0 M in diethyl ether, 79 mL, 158 mmol) dropwise until the solution turned yellow and gas evolution ceased. The reaction was then concentrated under reduced pressure to give methyl 5-oxo-5,6,7,8-tetrahydronaphthalene-2-carboxylate (10.72 g, 52.5 mmol, 100% yield) as a brown solid. MS ESI calcd for C12H12O3 [M+H]+ 205, found 205. 1H NMR (500 MHz, DMSO) δ 7.94 (d, J=8.1 Hz, 1H), 7.91 (s, 1H), 7.85 (dd, J=8.1, 1.6 Hz, 1H), 3.86 (s, 3H), 2.99 (t, J=6.0 Hz, 2H), 2.66-2.61 (m, 2H), 2.09-2.00 (m, 2H).

Workup

  1. concentrationThe reaction was then concentrated under reduced pressure

Sources & evidence

ORD record
ord-b0aec3d4d7cd4f799ec65c06601bc8a2
Source dataset
uspto-grants-2014_08
Patent number
US08796310B2

Reaction notes

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