Water → HCID 10664234、化合物

HRID 1107636ノート

反応式

HRID 1107636 の反応式
[CH2:1]([O:8][C:9]1[C:18]2[C:13](=[CH:14][C:15](Br)=[CH:16][CH:17]=2)[CH:12]=[C:11]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:25]([Cu])#[N:26].O>CN(C=O)C>[CH2:1]([O:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([C:25]#[N:26])=[CH:16][CH:17]=2)[CH:12]=[C:11]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 962WaterHCID 10667770Ethyl 4-(benzyloxy)-7-bromo-2-naphthoateHCID 178418546HCID 178418546、化合物

生成物 1

HCID 10664234HCID 10664234、化合物収率 74.3%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
25 °C

実験手順

A solution of 12 (9.46 g, 27.2 mmol) in anhydrous DMF (12.6 mL) under Ar was treated with CuCN (2.92 g, 32.6 mmol, 1.2 equiv) and the mixture was warmed at reflux for 20 h. The reaction mixture was cooled to 25° C. and poured into 250 mL of H2O to which FeCl3 (5.29 g, 32.6 mmol, 1.2 equiv) was added with swirling. The solution was extracted with EtOAc (3×200 mL) and the combined organic layers were washed with saturated aqueous NaCl, dried (MgSO4) and concentrated. Recrystallization from 20% EtOAc-hexane provided 13 (6.70 g, 9.00 g theoretical, 74%) as a white solid. Chromatography (SiO2, 4×20 cm, 10% EtOAc-hexane) of the crystallization mother liquors afforded additional 13 (2.00 g, 22%, 96% combined) as white solid: mp 125° C. (needles, EtOH); 1H NMR (CDCl3, 250 MHz) δ8.43 (d, 1H, J=8.7 Hz), 8.29 (s, 1H), 8.25 (s, 1H), 7.69 (dd, 1H, J=1.6, 8.7 Hz), 7.66 (s, 1H), 7.56-7.39 (m, 5H), 5.32 (s, 2H), 4.46 (q, 2H, J=7.2 Hz), 1.46 (t, 3H, J=7.1 Hz); 13C NMR (CDCl3, 62.5 MHz) δ165.9, 154.3, 135.9, 134.6, 132.3, 129.8, 128.6, 128.3, 128.2, 127.8, 127.5, 123.8, 123.2, 118.6, 110.7, 106.9, 70.5, 61.5, 14.3; IR (KBr) vmax 2994, 2226, 1711, 1577, 1502, 1284, 1252, 1093, 1029, 916, 827 cm-1 ; FABHRMS (NBA) m/z 332.1276 (M+ +H, C21H17NO3 requires 332.1287).

後処理

  1. temperaturethe mixture was warmed
  2. temperatureat reflux for 20 h
  3. additionwas added
  4. extractionThe solution was extracted with EtOAc (3×200 mL)
  5. washthe combined organic layers were washed with saturated aqueous NaCl
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. customRecrystallization from 20% EtOAc-hexane

出典と根拠

ORDレコード
ord-5649c9fec26940c7a2f1f7ab7041f772
出典データセット
uspto-grants-2000_05
特許番号
US06060608

反応ノート

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