(E)-3-[5-(5-methyl-2-phenyl-4-oxazolylmethoxy)-2-benzofuranyl]-2-propen-1-ol → 3-[5-(5-Methylphenyl-4-oxazolylmethoxy)-2-benzofuranyl]propanol

HRID 1062Notes

Reaction equation

HRID 1062 reaction equation
C[C:2]1[O:6][C:5](C2C=CC=CC=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:16]=[CH:17][C:18]2[O:22][C:21](/[CH:23]=[CH:24]/[CH2:25][OH:26])=[CH:20][C:19]=2[CH:27]=1>O1CCCC1.[C].[Pd]>[CH3:20][C:19]1[CH:18]=[CH:17][CH:16]=[C:15]([CH:13]([C:3]2[N:4]=[CH:5][O:6][CH:2]=2)[O:14][C:15]2[CH:16]=[CH:17][C:18]3[O:22][C:21]([CH2:23][CH2:24][CH2:25][OH:26])=[CH:20][C:19]=3[CH:27]=2)[CH:27]=1

Participants

4

Reactant 1

HCID 19694371(E)-3-[5-(5-methyl-2-phenyl-4-oxazolylmethoxy)-2-benzofuranyl]-2-propen-1-ol

Product 1

HCID 196943823-[5-(5-Methylphenyl-4-oxazolylmethoxy)-2-benzofuranyl]propanolYield 93%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (E)-3-[5-(5-methyl-2-phenyl-4-oxazolylmethoxy)-2-benzofuranyl]-2-propen-1-ol (2.00 g) in tetrahydrofuran (100 ml), palladium-carbon (5%, 0.30 g) was added, followed by catalytic reduction at room temperature and under an atmospheric pressure of 1 atm. After the catalyst was filtered off, the filtrate was concentrated to yield 3-[5-(5-methylphenyl-4-oxazolylmethoxy)-2-benzofuranyl]propanol (yield 93%), which was then recrystallized from acetone-isopropyl ether to yield colorless prisms having a melting point of 101° to 102° C.

Workup

  1. customfollowed by catalytic reduction at room temperature and under an atmospheric pressure of 1 atm
  2. filtrationAfter the catalyst was filtered off
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-a0b0409b86cb49f38ebdef232d24438a
Source dataset
uspto-grants-1998_03
Patent number
US05723479

Reaction notes

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