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

HRID 264112Notes

Reaction equation

HRID 264112 reaction equation
[CH2:1]([C:13]1[CH:17]=[C:16]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[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(C1ON=C(CC2C=CC=CC=2)C=1)CCCCCCCCCCC.C([Li])CCC.[C:54](=[O:56])=[O:55].C(C1ON=C(C(C2C=CC=CC=2)C(O)=O)C=1)CCCCCCCCCCC>O1CCCC1>[CH2:1]([C:13]1[CH:17]=[C:16]([CH:18]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:54]([OH:56])=[O:55])[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

7

Reactant 5

HCID 280Carbon Dioxide2×HCID 105232775-Dodecyl-alpha-phenyl-3-isoxazole acetic acidHCID 105682385-Dodecyl-3-(phenylmethyl)isoxazoleHCID 105923395-Benzyl-3-dodecylisoxazoleHCID 178418339Butyllithium

Product 1

HCID 108330563-Dodecyl-alpha-phenyl-5-isoxazole acetic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a cold (-78° C.), stirred suspension of 3-dodecyl-5-(phenylmethyl)isoxazole and 5-dodecyl-3-(phenylmethyl)isoxazole (1.64 g, 0.00500 mol) in dry tetrahydrofuran (150 mL) was added dropwise over 3 minutes a 2.06M solution (5.0 mL, 0.010 mol) of n-butyl lithium in hexanes, and the mixture was stirred for 80 minutes under nitrogen. The resulting orange solution was poured into freshly crushed dry ice (~300 g), the mixture was covered with parafilm with a small hole to allow CO2 (g) to escape, and allowed to warm to room temperature over 3 hours. The residue was partitioned between ether and 0.1M HCl. The organic layer was washed (saturated NaCl), dried (MgSO4), and rotoevaporated to a yellow oil. The oil was dissolved in petroleum ether (50 mL). A solid crystallized. It was filtered off and dried in vacuo to give a white solid containing the title compound and 5-dodecyl-α-phenyl-3-isoxazole acetic acid; yield 1.70 g (91%); mp 88°-97° C.

Workup

  1. stirringthe mixture was stirred for 80 minutes under nitrogen
  2. temperatureto warm to room temperature over 3 hours
  3. customThe residue was partitioned between ether and 0.1M HCl
  4. washThe organic layer was washed (saturated NaCl)
  5. dry with materialdried (MgSO4)
  6. dissolutionThe oil was dissolved in petroleum ether (50 mL)
  7. customA solid crystallized
  8. filtrationIt was filtered off
  9. customdried in vacuo
  10. customto give a white solid

Sources & evidence

ORD record
ord-96481a6d47f54c0988e9667632b27567
Source dataset
uspto-grants-1997_07
Patent number
US05646170

Reaction notes

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