Hydrochloric Acid → 3-Dodecyl-5-methylisoxazole

HRID 264106Notes

Reaction equation

HRID 264106 reaction equation
Br[CH2:2][C:3]1[O:7][N:6]=[C:5]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH:4]=1.[BH4-].[Na+].Cl>CS(C)=O>[CH2:8]([C:5]1[CH:4]=[C:3]([CH3:2])[O:7][N:6]=1)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 105443765-(Bromomethyl)-3-dodecylisoxazole

Product 1

HCID 104913863-Dodecyl-5-methylisoxazole

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A suspension of 5-(bromomethyl)-3-dodecylisoxazole (9.99 g, 0.0302 mol) in dimethylsulfoxide (100 mL) was warmed to give a cloudy solution and allowed to cool. When the temperature reached +35° C., sodium borohydride (1.2 g, 0.032 mol) was added in one portion, and the mixture was stirred for 3 days under nitrogen at room temperature. The mixture was poured into 0.1M HCl (900 mL) and extracted with ether. The organic layer was washed (saturated NaCl), dried (MgSO4), and rotoevaporated. The residue was chromatographed on silica gel (160 g, 70-230 mesh) using petroleum ether-acetone (29:1, 10×200 mL) as eluent. Fraction 6 was rotoevaporated and dried in vacuo to give a white solid; yield 3.96 g (52%); mp 35°-38° C.

Workup

  1. temperaturewas warmed
  2. customto give a cloudy solution
  3. temperatureto cool
  4. customreached +35° C.
  5. extractionextracted with ether
  6. washThe organic layer was washed (saturated NaCl)
  7. dry with materialdried (MgSO4)
  8. customThe residue was chromatographed on silica gel (160 g, 70-230 mesh)
  9. customdried in vacuo
  10. customto give a white solid

Sources & evidence

ORD record
ord-8771b1b62d9f40e3834d67fd7aad81cb
Source dataset
uspto-grants-1997_07
Patent number
US05646170

Reaction notes

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