Benzaldehyde → Dicinnamoylmethane

HRID 77635

反応式

HRID 77635 の反応式
[CH3:1][C:2](=[O:7])[CH2:3][C:4](=[O:6])[CH3:5].[CH:8](=O)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.B(OCCCC)(OCCCC)O[CH2:18][CH2:19][CH2:20]C.[CH2:32](N)[CH2:33][CH2:34][CH3:35].Cl>C(OCC)(=O)C>[C:9]1([CH:8]=[CH:1][C:2](=[O:7])[CH2:3][C:4](=[O:6])[CH:5]=[CH:35][C:34]2[CH:20]=[CH:19][CH:18]=[CH:32][CH:33]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

参加物

7

反応物 5

HCID 240BenzaldehydeHCID 313Hydrochloric AcidHCID 8007ButylamineHCID 12712Tributyl borateHCID 31261Acetylacetone

生成物 1

HCID 390472Dicinnamoylmethane収率 162.8%

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 2,4-pentanedione (2, 1.05 ml, 10.0 mmol) and stirred for 18 hr at room temperature under a nitrogen atmosphere. A solution of dry ethyl acetate (10 ml), benzaldehyde (1b, 2.05 g, 20.2 mmol) and tributyl borate (11.00 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 extracted into ethyl acetate, washed with saturated sodium chloride, dried over magnesium sulfate, filtered and evaporated to afford a solid. The crude solid was triturated with methanol to give 0.90 g (33%) of a yellow solid: mp 140-142° C. [expected mp 139-140° C.]; 1H NMR: δ 5.84 (s, 1H), 6.62 (d, 2H, J=15.7 Hz), 7.39 (m, 6H), 7.54 (dd, 4H, J=7.4, 4.0 Hz), 7.66 (d, 2H, J=15.9 Hz), 15.85 (s, 1H); 13C NMR: δ 101.6, 124.1, 128.0, 128.9, 130.0, 135.0, 140.5, 183.2.

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. extractionThe resulting mixture was extracted into ethyl acetate
  8. washwashed with saturated sodium chloride
  9. dry with materialdried over magnesium sulfate
  10. filtrationfiltered
  11. customevaporated
  12. customto afford a solid
  13. customThe crude solid was triturated with methanol

出典と根拠

ORDレコード
ord-998f773493e04693bd67be3f292a293a
出典データセット
uspto-grants-2014_09
特許番号
US08841326B2

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