Toluene → 4-Cyclohexylmethyloxy-3-(naphthalen-2-yl)benzaldehyde

HRID 2378538Notes

Reaction equation

[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1B(O)O.Br[C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][C:22]=1[O:23][CH2:24][CH:25]1[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1)[CH:18]=[O:19].C(=O)([O-])[O-].[Na+].[Na+].C1(C)C=CC=CC=1>CO.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(OCC)(=O)C>[CH:25]1([CH2:24][O:23][C:22]2[CH:21]=[CH:20][C:17]([CH:18]=[O:19])=[CH:16][C:15]=2[C:2]2[CH:3]=[CH:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH:1]=2)[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]1

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of 2-naphthaleneboronic acid (535 mg) in methanol (5.0 ml), Intermediate 25 (1.16 g), and 2 M aqueous sodium carbonate (0.9 ml) were added with toluene (10.0 ml) and tetrakistriphenylphosphinepalladium(0) [hereinafter abbreviated as “(Ph3P)4Pd”] (116 mg, Nakarai Tecs), and stirred at 80° C. for 17 hours. The reaction mixture was added with ethyl acetate (100 ml), and washed successively with saturated aqueous sodium hydrogencarbonate, saturated aqueous ammonium chloride and saturated brine. The organic layer was dried, and then the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography (hexane:ethyl acetate=10:1) to obtain the title compound (Compound No. C-1, 345 mg).

Workup

washwashed successively with saturated aqueous sodium hydrogencarbonate, saturated aqueous ammonium chloride and saturated brine
customThe organic layer was dried
customthe solvent was evaporated under reduced pressure
customThe residue was purified by flash column chromatography (hexane:ethyl acetate=10:1)

Sources & evidence

ORD record: ord-2fe814480dbc498ba039e6e094468d19
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07470807B2

Reaction notes

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