MeOH tetrahydrofuran → 3-(3-Carbomethoxyphenyl)methyl-6-hydroxy-4-chromanone

HRID 1886089ノート

反応式

HRID 1886089 の反応式
C([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[O:15][CH2:14][C:13](=[CH:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([OH:28])=[O:27])[CH:21]=1)[C:12]2=[O:29])C1C=CC=CC=1.[CH2:30]1COCC1.CO>[Pd]>[C:26]([C:22]1[CH:21]=[C:20]([CH2:19][CH:13]2[C:12](=[O:29])[C:11]3[C:16](=[CH:17][CH:18]=[C:9]([OH:8])[CH:10]=3)[O:15][CH2:14]2)[CH:25]=[CH:24][CH:23]=1)([O:28][CH3:30])=[O:27]

参加物

4

反応物 2

HCID 21899815MeOH tetrahydrofuranHCID 545697246-Benzyloxy-3-(3-carboxyphenylmethylene)-4-chromanone

生成物 1

HCID 190914643-(3-Carbomethoxyphenyl)methyl-6-hydroxy-4-chromanone収率 63%

試薬・触媒・溶媒 1

HCID 23938Palladium触媒

反応条件

温度
0 °C

実験手順

To a solution of 6-benzyloxy-3-)3-carboxyphenylmethylene)-4-chromanone from Step 2 (1.54 g, 3.8 mmol) in 40 ml THF/MeOH (1:3) was added 150 mg of 10% Pd/C. The mixture was hydrogenated at 40 psi for 20 hr. The mixture was filtered through celite. The filtrate was evaporated to dryness and redissolved in THF. The THF solution was cooled to 0° C. and diazomethane was added until no acid remained. Then HOAc was added. The mixture was evaporated to give an oil which was chromatographed on silica gel and eluted with 40% EtOAc/hexane to give 750 mg (63%) of the title compound.

後処理

  1. filtrationThe mixture was filtered through celite
  2. customThe filtrate was evaporated to dryness
  3. dissolutionredissolved in THF
  4. additiondiazomethane was added until no acid
  5. additionThen HOAc was added
  6. customThe mixture was evaporated
  7. customto give an oil which
  8. customwas chromatographed on silica gel
  9. washeluted with 40% EtOAc/hexane

出典と根拠

ORDレコード
ord-868f1ff3530a48ca81e46e55f6c0116d
出典データセット
uspto-grants-1992_09
特許番号
US05149703

反応ノート

読み込み中…