Water → HCID 10664234, 화합물

HRID 1107636노트

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HRID 1107636 반응식
[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

참가 물질

5

반응물 3

HCID 962WaterHCID 10667770Ethyl 4-(benzyloxy)-7-bromo-2-naphthoateHCID 178418546HCID 178418546, 화합물

생성물 1

HCID 10664234HCID 10664234, 화합물수율 74.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
25 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-5649c9fec26940c7a2f1f7ab7041f772
출처 데이터셋
uspto-grants-2000_05
특허 번호
US06060608

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