(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 1859319Notes

Reaction equation

HRID 1859319 reaction equation
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

Participants

4

Reactant 1

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

(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.

Workup

  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)

Sources & evidence

ORD record
ord-2e1e1173b0914ae8bba9b8f307b31537
Source dataset
uspto-grants-2000_11
Patent number
US06153768

Reaction notes

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