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

HRID 860544ノート

反応式

HRID 860544 の反応式
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

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-4847029cf3dd434b94ed0db7efc82491
出典データセット
uspto-grants-2006_12
特許番号
US07153875B2

反応ノート

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