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

HRID 77636

反応式

HRID 77636 の反応式
[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

参加物

6

反応物 4

HCID 240BenzaldehydeHCID 8007ButylamineHCID 12712Tributyl borateHCID 699493-Methyl-2,4-pentanedione

生成物 1

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

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-3d438f05a2d9468c92e3939d32888650
出典データセット
uspto-grants-2014_09
特許番号
US08841326B2

関連ノート

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