Phloroglucinol → 5,7-Dihydroxy-4-propylcoumarin

HRID 1185

反応式

HRID 1185 の反応式
[C:1]1([CH:9]=[C:7]([OH:8])[CH:6]=[C:4]([OH:5])[CH:3]=1)[OH:2].[C:10]([CH2:15][C:16](OCC)=[O:17])(=O)[CH2:11][CH2:12][CH3:13].FC(F)(F)S(O)(=O)=O>O>[OH:2][C:1]1[CH:9]=[C:7]([OH:8])[CH:6]=[C:4]2[C:3]=1[C:10]([CH2:11][CH2:12][CH3:13])=[CH:15][C:16](=[O:17])[O:5]2

参加物

5

反応物 3

HCID 359PhloroglucinolHCID 62406Trifluoromethanesulfonic acidHCID 238498Ethyl 3-oxohexanoate

生成物 1

HCID 53912605,7-Dihydroxy-4-propylcoumarin収率 99.1%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A suspension of anhydrous phloroglucinol (20.0 g, 0.159 mol) in ethyl butrylacetate (26.3 g; 0.167 mol) was added over 30 min to 50 g of constantly stirred trifluoromethanesulfonic acid cooled in an ice bath. A drying tube was then fined to the reaction vessel and the mixture was stirred for 16h at 25° C., after which the resulting thick paste was combined with ice (200 g) and water (300 mL) with brisk stirring. After 30 min the solid material was collected by vacuum filtration and recrystallised from 95% ethanol to yield coumarin 15 (34.7 g; 99%) as lemon yellow crystals. mp 236°-238° C. 1H NMR (CDCl3 /CD3OD 3:1): δ6.13(1H, d; J =2.3 Hz), 6.04(1H, d; J=2.3 Hz), 5.68(1H, s), 2.76(2H, t; J=7.4 Hz), 1.47(2H, tq; J =7.7, 7.4 Hz), 0.82(3H, t; J =7.7 Hz). 13C NMR (CDCl3 /CD3OD 3:1): δ163.1, 160.7, 160.6, 157.3, 156.7, 107.8, 102.5, 99.2, 95.0, 37.7, 22.5, 13.4. Anal. calc. for C12H12O4.(H2O): C, 60.50; H, 5.92. Found: C, 60.47; H, 5.92.

後処理

  1. temperaturecooled in an ice bath
  2. customA drying tube was then fined to the reaction vessel
  3. filtrationAfter 30 min the solid material was collected by vacuum filtration
  4. customrecrystallised from 95% ethanol

出典と根拠

ORDレコード
ord-66f1b1423ff84fd0aecb09103bf3af98
出典データセット
uspto-grants-1998_03
特許番号
US05723631

関連ノート

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