Potassium Carbonate → 6-[3-(1-Adamantyl)-4-methoxyphenyl]-2-naphthaldehyde

HRID 860544Notes

Reaction equation

HRID 860544 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([CH:12]=[O:13])[CH:6]=[CH:5]2.[C:14]12([C:24]3[CH:25]=[C:26](B(O)O)[CH:27]=[CH:28][C:29]=3[O:30][CH3:31])[CH2:23][CH:18]3[CH2:19][CH:20]([CH2:22][CH:16]([CH2:17]3)[CH2:15]1)[CH2:21]2.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.O.C(OCC)(=O)C>[C:14]12([C:24]3[CH:25]=[C:26]([C:2]4[CH:3]=[C:4]5[C:9](=[CH:10][CH:11]=4)[CH:8]=[C:7]([CH:12]=[O:13])[CH:6]=[CH:5]5)[CH:27]=[CH:28][C:29]=3[O:30][CH3:31])[CH2:15][CH:16]3[CH2:17][CH:18]([CH2:19][CH:20]([CH2:22]3)[CH2:21]1)[CH2:23]2

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 134770296-Bromonaphthalene-2-carbaldehydeHCID 231485923-(1-Adamantyl)-4-methoxyphenylboronic acid

Product 1

HCID 865860366-[3-(1-Adamantyl)-4-methoxyphenyl]-2-naphthaldehydeYield 82%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 6-bromo-2-naphthaldehyde (1.17 g, 4.98 mmol, see Example 3c), 3-(1-adamantyl)-4-methoxyphenyl boronic acid (1.57 g, 5.48 mmol, prepared in a manner similar to that described in Example 3b.) and potassium carbonate (1.55 g, 11.20 mmol) in 75 mL of toluene and water (4 mL) was degassed with argon for 30 minutes . Tetrakis(triphenyl phosphine)palladium(0) (0.575 g, 0.50 mmol) was added and the mixture heated at reflux for 18 hours. The solution was cooled to room temperature, diluted with ethyl acetate and washed successively with water and brine, dried over anhydrous magnesium sulfate, filtered and evaporated. The residue was purified on silica gel (eluent: hexane:CH2Cl2, 3:2 to 1:1) to give 1.6 g of 6-[3-(1-adamantyl)-4-methoxyphenyl]-2-naphthaldehyde (82%) as a solid. 1H NMR (300 MHz; CDCl3): δ 1.80 (s, 6H), 2.10–2.17(m, 9H), 3.90 (s, 3H), 6.99 (d, J=8.1 Hz, 1H), 7.52–7.60 (m, 2H), 7.82 (d, J=8.4 Hz, 1H), 7.95–8.02 (m, 4H), 8.32 (s, 1H), 10.13 (s, 1H).

Workup

  1. customprepared in a manner similar to
  2. temperaturethe mixture heated
  3. temperatureat reflux for 18 hours
  4. washwashed successively with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified on silica gel (eluent: hexane:CH2Cl2, 3:2 to 1:1)

Sources & evidence

ORD record
ord-4847029cf3dd434b94ed0db7efc82491
Source dataset
uspto-grants-2006_12
Patent number
US07153875B2

Reaction notes

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