Water → 2-[6-(3-[1-Adamantyl]-4-methoxyphenyl)-2-naphthyl]-2-hydroxy-acetonitrile

HRID 860569ノート

反応式

HRID 860569 の反応式
[C:1]12([C:11]3[CH:12]=[C:13]([C:19]4[CH:20]=[C:21]5[C:26](=[CH:27][CH:28]=4)[CH:25]=[C:24]([CH:29]=[O:30])[CH:23]=[CH:22]5)[CH:14]=[CH:15][C:16]=3[O:17][CH3:18])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.C[Si]([C:35]#[N:36])(C)C.O>C(Cl)Cl.[Zn+2].[I-].[I-]>[C:1]12([C:11]3[CH:12]=[C:13]([C:19]4[CH:20]=[C:21]5[C:26](=[CH:27][CH:28]=4)[CH:25]=[C:24]([CH:29]([OH:30])[C:35]#[N:36])[CH:23]=[CH:22]5)[CH:14]=[CH:15][C:16]=3[O:17][CH3:18])[CH2:8][CH:7]3[CH2:6][CH:5]([CH2:4][CH:3]([CH2:9]3)[CH2:2]1)[CH2:10]2

参加物

6

反応物 3

HCID 962WaterHCID 82115Trimethylsilyl cyanideHCID 865860366-[3-(1-Adamantyl)-4-methoxyphenyl]-2-naphthaldehyde

生成物 1

HCID 865860482-[6-(3-[1-Adamantyl]-4-methoxyphenyl)-2-naphthyl]-2-hydroxy-acetonitrile収率 80%

試薬・触媒・溶媒 2

HCID 9883512zinc(II)iodide触媒HCID 6344Dichloromethane溶媒

実験手順

To a suspension of 6-[3-(1-adamantyl)-4-methoxyphenyl]-2-naphthaldehyde (0.4 g, 1.01 mmol) and ZnI2 (0.07 mg, 0.02 mmol) in anhydrous CH2Cl2 (5 mL) stirring at 0–5° C. under an argon atmosphere was added trimethylsilylcyanide (0.16 mL, 1.18 mmol). The reaction mixture was stirred for 1.0 hour at 0–5° C. before it was allowed to warm to room temperature and stirred for 26 hours. It was poured into water, extracted with CH2Cl2. After removal of the solvent, the residue was dissolved in 1,3-dioxolane (10 mL) and 2N HCl added. After stirring at room temperature for 1.5 hours, it was poured into water, extracted with EtOAc, washed with water, brine and recrystallized from hexane/CH2Cl2 to afford 2-[6-(3-[1-adamantyl]-4-methoxyphenyl)-2-naphthyl]-2-hydroxy-acetonitrile as an orange powder 0.340 mg (80%). 1H NMR (300 MHz; CDCl3): δ 1.80 (s, 6H), 2.10–2.18 (m, 9H), 2.86 (s, 1H), 3.90 (s, 3H), 5.71 (s, 1H), 6.99 (d, J=8.4 Hz, 1H), 7.51–7.61 (m, 3H), 7.78–7.82 (m, 1H), 7.90–8.02 (m, 4H).

後処理

  1. stirringThe reaction mixture was stirred for 1.0 hour at 0–5° C. before it
  2. stirringstirred for 26 hours
  3. extractionextracted with CH2Cl2
  4. customAfter removal of the solvent
  5. dissolutionthe residue was dissolved in 1,3-dioxolane (10 mL)
  6. addition2N HCl added
  7. stirringAfter stirring at room temperature for 1.5 hours
  8. additionit was poured into water
  9. extractionextracted with EtOAc
  10. washwashed with water, brine
  11. customrecrystallized from hexane/CH2Cl2

出典と根拠

ORDレコード
ord-0b2c77bc30fd4e4fa012a1b04b4fa007
出典データセット
uspto-grants-2006_12
特許番号
US07153875B2

反応ノート

読み込み中…