苯甲醛 → 4-Methyl-1,7-diphenyl-1,6-heptadiene-3,5-dione

HRID 77636

反应方程式

HRID 77636 反应方程式
[CH3:1][CH:2]([C:6](=[O:8])[CH3:7])[C:3](=[O:5])[CH3:4].[CH:9](=O)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.B(OCCCC)(OCCCC)O[CH2:19][CH2:20][CH2:21]C.[CH2:33](N)[CH2:34][CH2:35][CH3:36]>C(OCC)(=O)C>[CH3:1][CH:2]([C:6](=[O:8])[CH:7]=[CH:36][C:35]1[CH:21]=[CH:20][CH:19]=[CH:33][CH:34]=1)[C:3](=[O:5])[CH:4]=[CH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

参与物

6

反应物 4

HCID 240苯甲醛HCID 8007正丁胺HCID 12712硼酸三丁酯HCID 699493-甲基-2,4-戊二酮

产物 1

HCID 695017264-Methyl-1,7-diphenyl-1,6-heptadiene-3,5-dione收率 310%

试剂、催化剂与溶剂 1

HCID 8857乙酸乙酯溶剂

实验过程

Boric anhydride (0.49 g, 7.0 mmol) was combined with 3-methyl-2,4-pentanedione (5, 1.14 g, 10.0 mmol) and stirred for 24 hr at room temperature under a nitrogen atmosphere. A solution of ethyl acetate (10 ml), benzaldehyde (1b, 2.05 ml, 20.2 mmol) and tributyl borate (11.0 ml, 40.5 mmol) was added and the mixture stirred for 15 min at room temperature. Butylamine (0.20 ml, 2.0 mmol) was added dropwise over 30 min and stirring was continued for 24 hr at room temperature. The resulting mixture was filtered to afford a solid. The crude solid was triturated with methanol to give 1.80 g (62%) of an orange solid: mp 154-157° C. [expected mp 154-157° C.]; 1H NMR: δ 2.17 (s, 3H), 7.12 (d, 2H, J=15.5 Hz), 7.38 (m, 6H), 7.58 (m, 4H), 7.74 (d, 2H, J=15.5 Hz); 13C NMR: δ 12.1, 106.2, 120.8, 182.1, 128.8, 129.9, 135.4, 141.3, 182.4. Anal. Calcd for C20H18O2: C, 82.73; H, 6.25. Found: C, 82.69; H, 6.36.

后处理

  1. stirringthe mixture stirred for 15 min at room temperature
  2. stirringstirring
  3. waitwas continued for 24 hr at room temperature
  4. filtrationThe resulting mixture was filtered
  5. customto afford a solid
  6. customThe crude solid was triturated with methanol

来源与证据

ORD记录
ord-3d438f05a2d9468c92e3939d32888650
来源数据集
uspto-grants-2014_09
专利号
US08841326B2

关联笔记

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