(3RS,4RS)-4-hydroxy-4-(3-hydroxyphenyl)-7-methoxymethyloxy-3-[4-(methoxymethyloxy)phenyl]-3-methyl-2,3-dihydro-4H-benzopyran → (3RS,4RS)-4-(3-hydroxyphenyl)-7-methoxymethyloxy-3-[4-(methoxymethyloxy)phenyl]-3-methyl-2,3-dihydro-4H-benzopyran

HRID 1859319ノート

反応式

HRID 1859319 の反応式
O[C:2]1([C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([OH:33])[CH:28]=2)[C:7]2[CH:8]=[CH:9][C:10]([O:12][CH2:13][O:14][CH3:15])=[CH:11][C:6]=2[O:5][CH2:4][C:3]1([C:17]1[CH:22]=[CH:21][C:20]([O:23][CH2:24][O:25][CH3:26])=[CH:19][CH:18]=1)[CH3:16]>CO.[Pd]>[OH:33][C:29]1[CH:28]=[C:27]([CH:2]2[C:7]3[CH:8]=[CH:9][C:10]([O:12][CH2:13][O:14][CH3:15])=[CH:11][C:6]=3[O:5][CH2:4][C:3]2([C:17]2[CH:18]=[CH:19][C:20]([O:23][CH2:24][O:25][CH3:26])=[CH:21][CH:22]=2)[CH3:16])[CH:32]=[CH:31][CH:30]=1

参加物

4

反応物 1

HCID 22123575(3RS,4RS)-4-hydroxy-4-(3-hydroxyphenyl)-7-methoxymethyloxy-3-[4-(methoxymethyloxy)phenyl]-3-methyl-2,3-dihydro-4H-benzopyran

生成物 1

HCID 22123578(3RS,4RS)-4-(3-hydroxyphenyl)-7-methoxymethyloxy-3-[4-(methoxymethyloxy)phenyl]-3-methyl-2,3-dihydro-4H-benzopyran収率 51.7%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 887Methanol溶媒

実験手順

(3RS,4RS)-4-Hydroxy-4-(3-hydroxyphenyl)-7-methoxymethyloxy-3-[4-(methoxymethyloxy)phenyl]-3-methyl-2,3-dihydro-4H-benzopyran (1.19 g, 2.63 mmol) prepared in Example 35 was dissolved in methanol (50 ml), and 10% Pd/C (200 mg) was slowly added dropwise thereto. The reaction mixture was stirred under hydrogen atmosphere for 12 hours and then filtered. The filtrate was concentrated under reduced pressure to remove the organic solvent. The concentrate was separated by column chromatography (n-hexane:ethyl acetate=8:1) to obtain 594 mg (yield: 50%) of the title compound as a colorless foam.

後処理

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. customto remove the organic solvent
  4. customThe concentrate was separated by column chromatography (n-hexane:ethyl acetate=8:1)

出典と根拠

ORDレコード
ord-2e1e1173b0914ae8bba9b8f307b31537
出典データセット
uspto-grants-2000_11
特許番号
US06153768

反応ノート

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