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

HRID 1289306Notes

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-bromonaphthalene-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 x), 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 x)
washthe organic layer was washed with brine
dry with materialdried over MgSO4
concentrationconcentrated in vacuo
customto give an oil

Sources & evidence

ORD record: ord-4d23b2bb8990472a86339d8efc69e885
Source dataset: uspto-grants-1998_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05747542

Reaction notes

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