5-Hydroxy-2,2-dimethyl-6-propionyl-10-propyl-2H,8H-pyrano[2,3-f]chromen-8-one → 5-Hydroxy-2,2-dimethyl-6-propanoyl-10-propyl-3,4-dihydropyrano[2,3-f]chromen-8-one

HRID 433968

反応式

HRID 433968 の反応式
[OH:1][C:2]1[C:11]([C:12](=[O:15])[CH2:13][CH3:14])=[C:10]2[C:5]([C:6]([CH2:17][CH2:18][CH3:19])=[CH:7][C:8](=[O:16])[O:9]2)=[C:4]2[O:20][C:21]([CH3:25])([CH3:24])[CH:22]=[CH:23][C:3]=12.[H][H]>C1(C)C=CC=CC=1.C(O)(C)C.[Pt]>[OH:1][C:2]1[C:11]([C:12](=[O:15])[CH2:13][CH3:14])=[C:10]2[C:5]([C:6]([CH2:17][CH2:18][CH3:19])=[CH:7][C:8](=[O:16])[O:9]2)=[C:4]2[O:20][C:21]([CH3:25])([CH3:24])[CH2:22][CH2:23][C:3]=12

参加物

5

反応物 2

HCID 54948815-Hydroxy-2,2-dimethyl-6-propionyl-10-propyl-2H,8H-pyrano[2,3-f]chromen-8-oneHCID 178418361HCID 178418361、化合物

生成物 1

HCID 52709555-Hydroxy-2,2-dimethyl-6-propanoyl-10-propyl-3,4-dihydropyrano[2,3-f]chromen-8-one収率 53%

試薬・触媒・溶媒 2

HCID 23939Platinum触媒HCID 21881414Toluene isopropyl alcohol溶媒

実験手順

A mixture of 5-hydroxy-2,2-dimethyl-6-propionyl-10-propyl-2H-pyrano[2,3-f]chromen-8-one (30) (5 g, 14.60 mmol) and sulfided platinum (5% on carbon, 1 g) in toluene/isopropyl alcohol (200/50 mL) was hydrogenated 16 h at room temperature under atmospheric pressure of hydrogen. The catalyst was filtered off and the filtrate concentrated under vacuum. The solid residue was crystallized from ethanol and re-crystallized from acetone to provide 2.66 g of 44a (53% yield). 1H NMR (CDCl3): 1.03 (t, J=7.5 Hz, 3H), 1.23 (t, J=7.5 Hz, 3H), 1.42 (s, 6H), 1.64 (m, 2H), 1.84 (t, J=6.5 Hz, 2H), 2.70 (t, J=6.5 Hz, 2H), 2.90 (m, 2H), 3.34 (q, J=7.0 Hz, 2H), 5.98 (s, 1H), 14.61 (s, 1H); 13C NMR (CDCl3): 8.45, 13.89, 16.42, 23.37, 26.62, 31.20, 38.13, 39.38, 77.60, 102.77, 103.43, 105.30, 110.22, 156.41, 157.29, 158.94, 159.76, 165.77, 206.67; IR: 1730 cm−1; MS (ACPI+): 345 (M+1); Anal. Calcd. for C20H24O5: C 69.75, H 7.02; Found C 70.03, H 7.18.

後処理

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate concentrated under vacuum
  3. customThe solid residue was crystallized from ethanol
  4. customre-crystallized from acetone

出典と根拠

ORDレコード
ord-7d60815ff1b9411894abe6665c27d528
出典データセット
uspto-grants-2003_12
特許番号
US06670383B2

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