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

HRID 77639

反応式

HRID 77639 の反応式
[CH2:1]([CH:8]([C:12](=[O:14])[CH3:13])[C:9](=[O:11])[CH3:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:15](=O)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.B(OCCCC)(OCCCC)O[CH2:25][CH2:26][CH2:27]C.[CH2:39](N)[CH2:40][CH2:41][CH3:42].Cl>C(OCC)(=O)C>[CH2:1]([CH:8]([C:9](=[O:11])[CH:10]=[CH:42][C:41]1[CH:27]=[CH:26][CH:25]=[CH:39][CH:40]=1)[C:12](=[O:14])[CH:13]=[CH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

7

反応物 5

HCID 240BenzaldehydeHCID 313Hydrochloric AcidHCID 8007ButylamineHCID 12712Tributyl borateHCID 977572,4-Pentanedione, 3-benzyl-

生成物 1

HCID 695017244-Benzyl-1,7-diphenyl-1,6-heptadiene-3,5-dione収率 313.8%

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-benzyl-2,4-pentanedione (8, 1.90 g, 10.0 mmol) and stirred for 48 hr at room temperature under a nitrogen atmosphere. A solution of dry 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 18 hr at room temperature. Hydrochloric acid (15 ml, 0.4 N) was warmed to 60° C., added to the mixture and stirring was continued for 1 hr. The resulting mixture was filtered to afford a solid. The crude solid was triturated with methanol to give 2.30 g (63%) of a yellow solid: mp 162-164° C. [expected mp 156-158° C.]; 1H NMR: δ 3.99 (s, 2H), 6.99 (d, 2H, J=15.6 Hz), 7.34 (m, 15H), 7.77 (d, 2H, J=15.2 Hz); 13C NMR: δ 31.8, 109.3, 120.8, 126.5, 127.8, 128.1, 128.8, 130.0, 135.3, 140.5, 141.9, 183.6.

後処理

  1. stirringthe mixture stirred for 15 min at room temperature
  2. stirringstirring
  3. waitwas continued for 18 hr at room temperature
  4. additionadded to the mixture
  5. stirringstirring
  6. waitwas continued for 1 hr
  7. filtrationThe resulting mixture was filtered
  8. customto afford a solid
  9. customThe crude solid was triturated with methanol

出典と根拠

ORDレコード
ord-2e9fa605a42840959f88d791f2c4ede4
出典データセット
uspto-grants-2014_09
特許番号
US08841326B2

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