Sodium borohydride → Benzenemethanol, 5-(4,5-dihydro-2-oxazolyl)-2-((5-(3-methyl-5-isoxazolyl)pentyl)oxy)-

HRID 1905512Notes

Reaction equation

HRID 1905512 reaction equation
[O:1]1[CH2:5][CH2:4][N:3]=[C:2]1[C:6]1[CH:23]=[CH:22][C:9]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]2[O:20][N:19]=[C:18]([CH3:21])[CH:17]=2)=[C:8]([CH:24]=[O:25])[CH:7]=1.[BH4-].[Na+]>CO.C(O)(=O)C.O>[O:1]1[CH2:5][CH2:4][N:3]=[C:2]1[C:6]1[CH:23]=[CH:22][C:9]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]2[O:20][N:19]=[C:18]([CH3:21])[CH:17]=2)=[C:8]([CH2:24][OH:25])[CH:7]=1

Participants

6

Reactant 2

HCID 4311764Sodium borohydrideHCID 5271233Benzaldehyde, 5-(4,5-dihydro-2-oxazolyl)-2-((5-(3-methyl-5-isoxazolyl)pentyl)oxy)-

Product 1

HCID 5271234Benzenemethanol, 5-(4,5-dihydro-2-oxazolyl)-2-((5-(3-methyl-5-isoxazolyl)pentyl)oxy)-Yield 99.4%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 1.2 g of 5-{5-[4-(4,5-dihydro-2-oxazolyl)-2-formylphenoxy]pentyl}-3-methylisoxazole (Example 70) in 10 ml of methanol was added in portions 0.2 g of sodium borohydride. The mixture was stirred for one hour, then treated with a few drops of glacial acetic acid and diluted to 50 ml with water. The solid product was collected, washed with aqueous methanol and recrystallized from ethyl acetate to give 1.2 g of 5-{5-[4-(4,5-dihydro-2-oxazolyl)-2-hydroxymethylphenoxy]pentyl}-3-methylisoxazole, m.p. 140°-141° C.

Workup

  1. customThe solid product was collected
  2. washwashed with aqueous methanol
  3. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-5474c644542d403f850d1cd7b53cee0e
Source dataset
uspto-grants-1989_06
Patent number
US04843087

Reaction notes

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