Water → Ethyl 4-(benzyloxy)-7-bromo-2-naphthoate

HRID 1107635노트

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HRID 1107635 반응식
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([OH:17])=[CH:7][C:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:9]2)=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH2:24](Br)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.O>CN(C=O)C>[CH2:24]([O:17][C:6]1[C:5]2[C:10](=[CH:11][C:2]([Br:1])=[CH:3][CH:4]=2)[CH:9]=[C:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:7]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 10613762HCID 10613762, 화합물

생성물 1

HCID 10667770Ethyl 4-(benzyloxy)-7-bromo-2-naphthoate수율 986.4%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
25 °C

실험 절차

A solution of 6 (8.04 g, 2.2 mmol) in anhydrous DMF (150 mL) under Ar was treated with K2CO3 (5.65 g, 40.9 mmol), benzyl bromide (5.59 g, 32.7 mmol, 1.2 equiv) and BU4NI (402 mg, 1.1 mmol, 0.04 equiv). After stirring for 11 h at 25° C., the reaction mixture was poured into H2O (200 mL) and extracted with EtOAc (3×200 mL). The combined organic layers were washed with saturated aqueous NaCl, dried (MgSO4) and concentrated. The resulting solid was recrystallized from 5% EtOAc-hexane to afford 12 (8.36 g, 10.49 g theoretical, 80%) as white needles. An additional 2.13 g (20%) of 12 was obtained by chromatography (SiO2, 4×20 cm, 10% EtOAc-hexane) of the crystallization mother liquors: mp 105° C. (needles, hexane); 1H NMR (CDCl3, 250 MHz) δ8.19 (d, 1H, J=8.8 Hz), 8.10 (s, 1H), 8.05 (d, 1H, J=1.8 Hz), 7.61 (dd, 1H, J=1.9, 8.9 Hz), 7.50 (m, 6H), 5.28 (s, 2H), 4.45 (q, 2H, J=7.1 Hz), 1.46 (t, 3H, J=7.1 Hz); 13C NMR (CDCl3, 100 MHz) δ166.5, 154.7, 136.4, 134.7, 130.8, 130.7, 129.1, 128.7, 128.3, 127.6, 126.3, 124.2, 122.5, 121.5, 104.6, 70.4, 61.4, 14.4; IR (KBr) vmax 2986, 1716, 1589, 1578, 1406, 1369, 1331, 1279, 1238, 1098, 1025, 962, 892, 816, 767, 725, 691 cm-1 ; FABHRS (NBA) m/z 384.0370 (M+, C20H17BrO3 requires 384.0361).

후처리

  1. extractionextracted with EtOAc (3×200 mL)
  2. washThe combined organic layers were washed with saturated aqueous NaCl
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe resulting solid was recrystallized from 5% EtOAc-hexane

출처 및 근거

ORD 기록
ord-89ba1954475e4030ae7f545938ac54fe
출처 데이터셋
uspto-grants-2000_05
특허 번호
US06060608

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