Potassium Carbonate → 4-[3-(1-Adamantyl)-4,5-methylenedioxyphenyl]-benzaldehyde

HRID 860524

反応式

HRID 860524 の反応式
[C:1]12([C:11]3[CH:12]=[C:13](Br)[CH:14]=[C:15]4[O:19][CH2:18][O:17][C:16]=34)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[CH:21]([C:23]1[CH:28]=[CH:27][C:26](B(O)O)=[CH:25][CH:24]=1)=[O:22].C(=O)([O-])[O-].[K+].[K+]>COCCOC.O.C(OCC)(=O)C.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:1]12([C:11]3[CH:12]=[C:13]([C:26]4[CH:27]=[CH:28][C:23]([CH:21]=[O:22])=[CH:24][CH:25]=4)[CH:14]=[C:15]4[O:19][CH2:18][O:17][C:16]=34)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2

参加物

8

反応物 3

HCID 11430Potassium CarbonateHCID 5910734-Formylphenylboronic AcidHCID 194297023-(1-Adamantyl)-4,5-methylenedioxybromobenzene

生成物 1

HCID 101554434-[3-(1-Adamantyl)-4,5-methylenedioxyphenyl]-benzaldehyde収率 85%

試薬・触媒・溶媒 4

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 80711,2-Dimethoxyethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A mixture of 3-(1-adamantyl)-4,5-methylenedioxy-1-bromobenzene (2.00 g, 5.97 mmol), 4-formylphenylboronic acid (1.07 g, 7.16 mmol) and potassium carbonate (1.86 g, 13.42 mmol) in 1,2-dimethoxyethane (50 mL) and water (2.5 mL) was degassed with argon for 30 minutes. Tetrakis(triphenylphosphine)palladium(0) (0.34 g, 0.298 mmol) was added and the mixture heated at reflux under argon overnight. The solution was cooled to room temperature, diluted with ethyl acetate (200 mL) and washed successively with water (100 mL) and brine (100 mL), dried over anhydrous magnesium sulfate, filtered and evaporated. The residue was purified on silica gel (eluent: hexane:ethyl acetate, 95:5) to give 1.82 g of 4-[3-(1-Adamantyl)-4,5-methylenedioxy phenyl]-benzaldehyde (85%). 1H NMR (500 MHz; CDCl3): δ 1.79 (s, 6H); 2.08 (s, 9H); 6.01 (s, 2H); 7.00 (d, J=2.0 Hz, 1H); 7.04 (d, J=2.0 Hz, 1H); 7.68 (d, J=8.1 Hz, 2H); 7.91 (d, J=8.1 Hz, 2H); 10.03 (s, 1H).

後処理

  1. customwas degassed with argon for 30 minutes
  2. temperaturethe mixture heated
  3. temperatureat reflux under argon overnight
  4. washwashed successively with water (100 mL) and brine (100 mL)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified on silica gel (eluent: hexane:ethyl acetate, 95:5)

出典と根拠

ORDレコード
ord-2c2ad17e4fa14963a579d3c92f029f61
出典データセット
uspto-grants-2006_12
特許番号
US07153875B2

関連ノート

読み込み中…