HCID 54418120, compound → HCID 15599362, compound

HRID 867461Notes

Reaction equation

HRID 867461 reaction equation
C([O:8][C:9]1[C:10]([CH:18]=[CH:19][C:20]2[N:21]([CH3:25])[CH:22]=[CH:23][N:24]=2)=[CH:11][C:12]2[O:16][CH2:15][CH2:14][C:13]=2[CH:17]=1)C1C=CC=CC=1>C(O)C.[Pd]>[CH3:25][N:21]1[CH:22]=[CH:23][N:24]=[C:20]1[CH2:19][CH2:18][C:10]1[C:9]([OH:8])=[CH:17][C:13]2[CH2:14][CH2:15][O:16][C:12]=2[CH:11]=1

Participants

4

Reactant 1

HCID 54418120HCID 54418120, compound

Product 1

HCID 15599362HCID 15599362, compoundYield 81.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Approximately a 1:1 ratio of cis and trans isomers of 1-(5-benzyloxy-2,3-dihydrobenzofuran-6-yl)-2-(1-methylimidazol-2-yl)ethene (104 mg, 0.3 mmoles) was hydrogenated in ethyl alcohol (15 ml) at room temperature using 10% Pd/C (15 mg) as a catalyst which was removed by suction filtration of the reaction mixture through a bed of celite. The catalyst bed was washed with ethyl alcohol (2×10 ml) and the filtrate was evaporated in vacuo to afford a white solid. Recrystallization from methlene chloride/n-hexane produced 6-(2-(1-methylimidazol-2-yl)ethyl)-5-hydroxy-2,3-dihydrobenzofuran as fine white crystals (60 mg, 79%). m.p. 190°-191° C.

Workup

  1. customwas removed by suction filtration of the reaction mixture through a bed of celite
  2. washThe catalyst bed was washed with ethyl alcohol (2×10 ml)
  3. customthe filtrate was evaporated in vacuo
  4. customto afford a white solid
  5. customRecrystallization from methlene chloride/n-hexane

Sources & evidence

ORD record
ord-65cfbc3169ee4a45b5a6351272e542cb
Source dataset
uspto-grants-1988_10
Patent number
US04775679

Reaction notes

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