Methanol → HCID 10936832, compound

HRID 1584350Notes

Reaction equation

HRID 1584350 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[O:7][C:8]([CH3:28])=[C:9]([CH2:11][O:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][C:21](OCC)=[O:22])=[CH:15][C:14]=2[O:26][CH3:27])[N:10]=1.[BH4-].[Na+].O1CCCC1.CO>O>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[O:7][C:8]([CH3:28])=[C:9]([CH2:11][O:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][CH2:21][OH:22])=[CH:15][C:14]=2[O:26][CH3:27])[N:10]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 10861958HCID 10861958, compound

Product 1

HCID 10936832HCID 10936832, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of ethyl 3-[4-[2-(2-furyl)-5-methyl-4-oxazolylmethoxy]-3-methoxyphenyl]propionate (20 g), sodium borohydride (9.8 g) and tetrahydrofuran (THF) (200 ml) was added dropwise methanol (50 ml) over 2 hours under reflux. The reaction mixture was poured into water, which was subjected to extraction with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4) and concentrated to yield 3-[4-[2-(2-furyl)-5-methyl-4-oxazolylmethoxy]-3-methoxyphenyl]propanol (15.5 g, 87%), which was recrystallized from ethyl acetate-hexane to give colorless prisms, m.p.99-100° C.

Workup

  1. temperatureunder reflux
  2. extractionwas subjected to extraction with ethyl acetate
  3. washThe ethyl acetate layer was washed with water
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-f234e11d9ec746ce952f5732ca423bbd
Source dataset
uspto-grants-1999_08
Patent number
US05932601

Reaction notes

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