HCID 131721745, compound → HCID 69961800, compound

HRID 429453Notes

Reaction equation

HRID 429453 reaction equation
[CH3:1][O:2][C:3](=[O:36])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C@H:12]2[C:21]3[C:16](=[CH:17][C:18]([O:22]CC4C=CC=CC=4)=[CH:19][CH:20]=3)[O:15][CH2:14][C@H:13]2[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[CH:8][CH:7]=1>O1CCCC1CO.C(O)=O.[Pd]>[CH3:1][O:2][C:3](=[O:36])[CH2:4][O:5][C:6]1[CH:7]=[CH:8][C:9]([C@H:12]2[C:21]3[C:16](=[CH:17][C:18]([OH:22])=[CH:19][CH:20]=3)[O:15][CH2:14][C@H:13]2[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[CH:10][CH:11]=1

Participants

4

Reactant 1

HCID 131721745HCID 131721745, compound

Product 1

HCID 69961800HCID 69961800, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 70238023HCID 70238023, compoundSolvent

Procedure

(+,−) cis [4-(7-Benzyloxy-3-phenyl-chroman-4-yl)-phenoxy]-acetic acid methyl ester(100 mg, 0.21 mmol) was dissolved in a solvent mixture of tetrahydrofuran-methanol-formic acid (8+1+1, 10 ml). The solution was added to a 5% Palladium on carbon catalyst (20 mg), and hydrogenated (1 atm.) overnight. The reaction mixture was filtered and evaporated to give a dark oil, which was dissolved and evaporated from EtOH (×3), triturated with toluene, and recrystallised from toluene.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customevaporated
  3. customto give a dark oil, which
  4. dissolutionwas dissolved
  5. customevaporated from EtOH (×3)
  6. customtriturated with toluene
  7. customrecrystallised from toluene

Sources & evidence

ORD record
ord-587b3c84f89b4237bf7e625a5333330b
Source dataset
uspto-grants-2001_11
Patent number
US06316494B1

Reaction notes

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