Acetic Acid → HCID 57682934, compound

HRID 494990Notes

Reaction equation

HRID 494990 reaction equation
[CH3:1][O:2][C:3]1[C:12]([CH2:13][CH:14]=[C:15]([CH3:17])[CH3:16])=[CH:11][C:6]2[N:7]=[C:8]([CH3:10])[O:9][C:5]=2[CH:4]=1.[BH4-].[Na+].C(O)(=O)C>O1CCCC1>[CH2:8]([NH:7][C:6]1[CH:11]=[C:12]([CH2:13][CH:14]=[C:15]([CH3:17])[CH3:16])[C:3]([O:2][CH3:1])=[CH:4][C:5]=1[OH:9])[CH3:10]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 57682868HCID 57682868, compound

Product 1

HCID 57682934HCID 57682934, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

231 mg of 6-methoxy-2-methyl-5-(3-methyl-2-butenyl)benzoxazole was dissolved in 5 ml of tetrahydrofuran under nitrogen atmosphere. Thereafter, 0.4 ml of a tetrahydrofuran solution containing 0.12 g of sodium borohydride and 0.1 ml of acetic acid was added to the reaction solution over 20 minutes, and the obtained mixture was stirred at room temperature overnight. The reaction solution was concentrated under a reduced pressure. A saturated ammonium chloride aqueous solution was added to the residue, followed by extraction with methylene chloride. The extract was washed with a saturated sodium chloride aqueous solution. The organic layer was dried over magnesium sulfate and then concentrated under a reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate), so as to obtain 80 mg of 2-ethylamino-5-methoxy-4-(3-methyl-2-butenyl)phenol containing a product whose structure was unknown. This compound was directly used in the following reaction without further purification.

Workup

  1. additionwas added to the reaction solution over 20 minutes
  2. concentrationThe reaction solution was concentrated under a reduced pressure
  3. additionA saturated ammonium chloride aqueous solution was added to the residue
  4. extractionfollowed by extraction with methylene chloride
  5. washThe extract was washed with a saturated sodium chloride aqueous solution
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. concentrationconcentrated under a reduced pressure
  8. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-887f18e4dd91421486159859ebd3bc65
Source dataset
uspto-grants-2009_05
Patent number
US07538123B2

Reaction notes

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