Toluene → Ethyl-6-[5,6,7,8-tetrahydro-5,5-dimethyl-naphth-7-yl]naphth-2-oate

HRID 1376

Reaction equation

Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:6]=[CH:5]2.C1(C)C=CC=CC=1.[CH3:24][C:25]1([CH3:38])[CH2:34][CH2:33][CH2:32][C:31]2[CH:30]=[C:29](B(O)O)[CH:28]=[CH:27][C:26]1=2.C(OCC)(=O)C>CO.C([O-])([O-])=O.[Na+].[Na+].CCCCCC>[CH2:15]([O:14][C:12]([C:7]1[CH:6]=[CH:5][C:4]2[C:9](=[CH:10][CH:11]=[C:2]([CH:33]3[CH2:32][C:31]4[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=4[C:25]([CH3:38])([CH3:24])[CH2:34]3)[CH:3]=2)[CH:8]=1)=[O:13])[CH3:16]

Participants

Conditions

Temperature: 80 °C

Procedure

To a degassed solution of 0.39 g (1.4 mmol) of ethyl 6-bromo-naphthalene-2-carboxylate and 3.0 mL of toluene, was added sequentially 49 mg (0.04 mmol) of tetrakis-triphenylphosphine palladium(0), 2.0 mL (2.0 mmol) of 1M sodium carbonate and then a solution of 0.32 g (1.6 mmol) of (5,6,7,8-tetrahydro-5,5-dimethylnaphth-2-yl)boronic acid (Compound B13) in 3.0 mL of MeOH. The reaction was heated at 80° C. for 6 h, diluted with 2N Na2CO3, and extracted with CH2Cl2 (2×), the organic layer was washed with brine, dried over MgSO4, and concentrated in vacuo to give an oil. Flash chromatography (silica, 5% ethyl acetate in hexane) of the crude material gave the title compound as a white solid.

Workup

extractionextracted with CH2Cl2 (2×)
washthe organic layer was washed with brine
dry with materialdried over MgSO4
concentrationconcentrated in vacuo
customto give an oil

Sources & evidence

ORD record: ord-97b20453788c4bc8828b820164729c18
Source dataset: uspto-grants-1998_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05723666

Linked notes

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