Hydrochloric Acid → HCID 86605730, compound

HRID 2221597Notes

Reaction equation

HRID 2221597 reaction equation
[CH:1]([C:3]1[CH:30]=[CH:29][C:6]([O:7][CH2:8][C:9]2[N:10]=[C:11]([C:15]3[CH:16]=[CH:17][C:18]([O:24][S:25]([CH3:28])(=[O:27])=[O:26])=[C:19]([CH:23]=3)[C:20]([O-:22])=[O:21])[O:12][C:13]=2[CH3:14])=[C:5]([O:31][CH3:32])[CH:4]=1)=[O:2].[CH2:33](O)C.[BH4-].[Na+].Cl>O1CCCC1>[OH:2][CH2:1][C:3]1[CH:30]=[CH:29][C:6]([O:7][CH2:8][C:9]2[N:10]=[C:11]([C:15]3[CH:16]=[CH:17][C:18]([O:24][S:25]([CH3:28])(=[O:27])=[O:26])=[C:19]([CH:23]=3)[C:20]([O:22][CH3:33])=[O:21])[O:12][C:13]=2[CH3:14])=[C:5]([O:31][CH3:32])[CH:4]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 4311764Sodium borohydrideHCID 86605731HCID 86605731, compound

Product 1

HCID 86605730HCID 86605730, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl (5-{4-[(4-formyl-2-methoxyphenoxy)methyl]-5-methyl-1,3-oxazol-2-yl}-2-methanesulfonyloxybenzoate (5.70 g) in tetrahydrofuran (100 mL)-ethanol (10 mL) was gradually added sodium borohydride (0.23 g) at 0° C. After stirring the reaction mixture at room temperature for 2 hrs, dilute hydrochloric acid was added to acidify the solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography, and eluted with ethyl acetate-hexane (5:1, v/v) to give methyl 5-{4-[(4-hydroxymethyl-2-methoxyphenoxy)methyl]-5-methyl-1,3-oxazol-2-yl}-2-methanesulfonyloxybenzoate as colorless crystals (4.02 g, yield 70%). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 126-127° C.

Workup

  1. customat 0° C
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. washeluted with ethyl acetate-hexane (5:1

Sources & evidence

ORD record
ord-93c26367b1a3401095adfc9e2385c515
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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