Carbon Dioxide → 3-Dodecyl-5-isoxazole acetic acid

HRID 2380513Notes

Reaction equation

HRID 2380513 reaction equation
[CH2:1]([C:13]1[CH:17]=[C:16]([CH3:18])[O:15][N:14]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].C([Li])CCC.[C:24](=[O:26])=[O:25]>O1CCCC1>[CH2:1]([C:13]1[CH:17]=[C:16]([CH2:18][C:24]([OH:26])=[O:25])[O:15][N:14]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

5

Reactant 3

HCID 280Carbon DioxideHCID 104913863-Dodecyl-5-methylisoxazoleHCID 178418339Butyllithium

Product 1

HCID 104941103-Dodecyl-5-isoxazole acetic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-75 °C

Procedure

To a cold (-75° C.), stirred suspension of 3-dodecyl-5-methylisoxazole (3.40 g, 0.0135 mol) in dry tetrahydrofuran (900 mL) was added in one portion a 1.6M solution (8.5 mL, 0.014 mol) of n-butyl lithium in hexanes, and the mixture was stirred for 1.5 hours. The mixture was poured onto freshly crushed dry ice and allowed to warm overnight. The mixture was rotoevaporated, and the residue was partitioned between petroleum ether and 0.5M NaOH. The aqueous layer was washed (petroleum ether), acidified with concentrated hydrochloric acid to pH ~1-2, and extracted (CHCl3). The extract was dried (MgSO4) and rotoevaporated to a waxy solid. The solid was recrystallized from toluene to give a white solid; yield 0.65 g (16%); mp 79°-80° C.

Workup

  1. stirringthe mixture was stirred for 1.5 hours
  2. temperatureto warm overnight
  3. customthe residue was partitioned between petroleum ether and 0.5M NaOH
  4. washThe aqueous layer was washed (petroleum ether)
  5. extractionextracted (CHCl3)
  6. dry with materialThe extract was dried (MgSO4)
  7. customThe solid was recrystallized from toluene
  8. customto give a white solid

Sources & evidence

ORD record
ord-26031ff77c434ae4bd5edc82cb8a0dd8
Source dataset
uspto-grants-1994_11
Patent number
US05366987

Reaction notes

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