Potassium Carbonate → 4-[3-(1-Adamantyl)-4-(t-butyldimethylsilyloxy)phenyl]-benzaldehyde

HRID 860549ノート

反応式

HRID 860549 の反応式
[CH:1]([C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1)=[O:2].[C:12]12([C:22]3[CH:23]=[C:24](Br)[CH:25]=[CH:26][C:27]=3[O:28][Si:29]([C:32]([CH3:35])([CH3:34])[CH3:33])([CH3:31])[CH3:30])[CH2:21][CH:16]3[CH2:17][CH:18]([CH2:20][CH:14]([CH2:15]3)[CH2:13]1)[CH2:19]2.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.CO.O.C(OCC)(=O)C.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:12]12([C:22]3[CH:23]=[C:24]([C:6]4[CH:7]=[CH:8][C:3]([CH:1]=[O:2])=[CH:4][CH:5]=4)[CH:25]=[CH:26][C:27]=3[O:28][Si:29]([C:32]([CH3:35])([CH3:34])[CH3:33])([CH3:30])[CH3:31])[CH2:13][CH:14]3[CH2:20][CH:18]([CH2:17][CH:16]([CH2:15]3)[CH2:21]1)[CH2:19]2

参加物

8

反応物 3

HCID 11430Potassium CarbonateHCID 5910734-Formylphenylboronic AcidHCID 107883163-(1-Adamantyl)-4-(t-butyldimethylsilyloxy)bromobenzene

生成物 1

HCID 113853054-[3-(1-Adamantyl)-4-(t-butyldimethylsilyloxy)phenyl]-benzaldehyde収率 78%

試薬・触媒・溶媒 4

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒HCID 21867641Toluene methanol溶媒

実験手順

A mixture of 4-formylphenyl boronic acid (0.301 g, 2.00 mmol), 3-(1-adamantyl)-4-(t-butyldimethylsilyloxy)bromobenzene (0.768 g, 1.82 mmol, prepared in a similar manner as described by Charpentier, B. et al. in J. Med. Chem. 1995, 38, 4993–5006) and potassium carbonate (0.757 g, 5.47 mmol) in 60 mL of toluene:methanol (4:1) and water (2 mL) was degassed with argon for 30 minutes. Tetrakis(triphenylphosphine) palladium(0) (0.422 g, 0.36 mmol) was added and the mixture heated at reflux for 19 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:EtOAc, 97:3) to give 0.500 g of 4-[3-(1-adamantyl)-4-(t-butyldimethylsilyloxy)phenyl]-benzaldehyde (78%) as a solid. 1H NMR (300 MHz; CDCl3): 0.38 (s, 6H), 1.07 (s, 9H), 1.79 (s, 6H), 2.10–2.17 (m, 9H), 6.89 (d, J=8.7 Hz, 1H), 7.34 (dd, J1=8.4 Hz, J2=2.4 Hz, 1H), 7.52 (d, J=2.4 Hz, 1H), 7.71 (d, J=8.1 Hz, 2H), 7.91 (d, J=8.1 Hz, 2H), 10.02 (brs, 1H).

後処理

  1. customprepared in a similar manner
  2. temperaturethe mixture heated
  3. temperatureat reflux for 19 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:EtOAc, 97:3)

出典と根拠

ORDレコード
ord-1c8da66cc81748a0a8a579bab108a655
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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