Ethanol → HCID 15171900, compound

HRID 256864Notes

Reaction equation

HRID 256864 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:16]#[C:17][C:18]2([CH3:32])[CH2:23][CH2:22][C:21]3[C:24]([CH3:31])=[C:25]([OH:30])[C:26]([CH3:29])=[C:27]([CH3:28])[C:20]=3[O:19]2)[CH:5]=[CH:6][C:7]=1[O:8]CC1C=CC=CC=1.C(O)C>[Pd].C(O)(=O)C>[OH:30][C:25]1[C:26]([CH3:29])=[C:27]([CH3:28])[C:20]2[O:19][C:18]([CH2:17][CH2:16][C:4]3[CH:3]=[C:2]([OH:1])[C:7]([OH:8])=[CH:6][CH:5]=3)([CH3:32])[CH2:23][CH2:22][C:21]=2[C:24]=1[CH3:31]

Participants

5

Reactant 2

HCID 702EthanolHCID 15171862HCID 15171862, compound

Product 1

HCID 15171900HCID 15171900, compoundYield 62.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 1 g of rac-3,4-dihydro-2-{[3-hydroxy-4-(phenylmethoxy)phenyl]ethynyl}-2,5,7,8-tetramethyl-2H-1-benzopyran-6-ol, 0.5 g of 5% palladium on carbon, 100 ml of ethanol and 10 ml of glacial acetic acid was hydrogenated at atmospheric pressure for 4.5 hours. The catalyst was filtered off and the filtrate was evaporated. The residue was partitioned between methylene chloride and saturated sodium bicarbonate solution. The organic layer was dried and evaporated and the residue was crystallized from ether/hexane to give 0.5 g of colorless crystals with m.p. 167°-170°.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate was evaporated
  3. customThe residue was partitioned between methylene chloride and saturated sodium bicarbonate solution
  4. customThe organic layer was dried
  5. customevaporated
  6. customthe residue was crystallized from ether/hexane

Sources & evidence

ORD record
ord-4669c0e4b053497baad3062e70a48a18
Source dataset
uspto-grants-1993_11
Patent number
US05260294

Reaction notes

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