Epichlorohydrin → 4-Benzyloxy-7-(2,3-epoxypropyloxy)coumarin

HRID 444214ノート

反応式

HRID 444214 の反応式
[CH2:1]([O:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([OH:19])=[CH:16][CH:17]=2)[O:12][C:11](=[O:20])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+].[CH2:23]([CH:25]1[O:27][CH2:26]1)Cl>C(O)C.O>[CH2:1]([O:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([O:19][CH2:23][CH:25]3[O:27][CH2:26]3)=[CH:16][CH:17]=2)[O:12][C:11](=[O:20])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

6

反応物 3

HCID 7835EpichlorohydrinHCID 14797Potassium HydroxideHCID 134084074-Benzyloxy-7-hydroxycoumarin

生成物 1

HCID 134084084-Benzyloxy-7-(2,3-epoxypropyloxy)coumarin

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒

実験手順

4-Benzyloxy-7-hydroxycoumarin (10.7 g, 0.041 mole) was dissolved in ethanol (200 ml) and a solution of potassium hydroxide (2.5 g) in water (10 ml) was added. Epichlorhydrin (40 ml) was added and the stirred mixture heated to reflux for 21/2 hr. After cooling, the solvent was removed in vacuo and the residue partitioned between water and ethyl acetate. Evaporation of the dried (MgSO4) organic phase gave the product as a white crystalline solid. Recrystallization from ethanol gave 11.1 g (83%) of material of m.p. 128°-129° C.; (Found; C, 70.48; H, 4.92; C19H16O5 requires; C, 70.36; H, 4.97%).

後処理

  1. temperaturethe stirred mixture heated
  2. temperatureto reflux for 21/2 hr
  3. temperatureAfter cooling
  4. customthe solvent was removed in vacuo
  5. customthe residue partitioned between water and ethyl acetate
  6. customEvaporation of the
  7. dry with materialdried (MgSO4) organic phase

出典と根拠

ORDレコード
ord-9d0ac0a5027940a7aa31852e5a9d8c75
出典データセット
uspto-grants-1981_04
特許番号
US04263299

反応ノート

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