(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 1859319노트

반응식

HRID 1859319 반응식
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

참가 물질

4

반응물 1

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

생성물 1

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

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 887Methanol용매

실험 절차

(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.

후처리

  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)

출처 및 근거

ORD 기록
ord-2e1e1173b0914ae8bba9b8f307b31537
출처 데이터셋
uspto-grants-2000_11
특허 번호
US06153768

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