Methyl chloroformate → HCID 59264806, compound

HRID 646459Notes

Reaction equation

HRID 646459 reaction equation
C([Li])CCC.[CH2:6]([O:13][C:14]1[CH:19]=[C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:17](Br)=[CH:16][C:15]=1[C:29]1[O:33][N:32]=[C:31]([CH3:34])[C:30]=1[C:35]1[CH:40]=[CH:39][C:38]([O:41][CH3:42])=[CH:37][CH:36]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.Cl[C:44]([O:46][CH3:47])=[O:45]>O1CCCC1>[CH3:47][O:46][C:44](=[O:45])[C:17]1[CH:16]=[C:15]([C:29]2[O:33][N:32]=[C:31]([CH3:34])[C:30]=2[C:35]2[CH:40]=[CH:39][C:38]([O:41][CH3:42])=[CH:37][CH:36]=2)[C:14]([O:13][CH2:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[CH:19][C:18]=1[O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 59264722HCID 59264722, compoundHCID 178418339Butyllithium

Product 1

HCID 59264806HCID 59264806, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-70 °C

Procedure

n-Butyl lithium (1001 μl) was added to a solution of 5-(2,4-bis-benzyloxy-5-bromo-phenyl)-4-(4-methoxy-phenyl)-3-methyl-isoxazole (154 mg, 0.28 mmol) in tetrahydrofuran (2.5 ml) under a nitrogen atmosphere at −78° C. Solution stirred at −70° C. for 30 minutes to give an orange solution. The ion was quenched with methyl chloroformate (100 μl, 3 eq) and allowed to warm to room temperature for 30 minutes. The solution was quenched with saturated aqueous ammonium chloride (5 ml). The mixture was extracted with ethyl acetate (3×5 ml). The combined extracts were washed with water (2×5 ml) and saturated aqueous sodium chloride solution (5 ml). The solution was dried over anhydrous magnesium sulphate and concentrated. The crude products were purified by column chromatography, silica, eluting with ethyl acetate in hexane (gradient 20% to 60% ethyl acetate) to give 2,4-Bis-benzyloxy-5-[4-(4-methoxy-phenyl)-3-methyl-isoxazol-5-yl]-benzoic acid methyl ester (72 mg).

Workup

  1. customto give an orange solution
  2. temperatureto warm to room temperature for 30 minutes
  3. customThe solution was quenched with saturated aqueous ammonium chloride (5 ml)
  4. extractionThe mixture was extracted with ethyl acetate (3×5 ml)
  5. washThe combined extracts were washed with water (2×5 ml) and saturated aqueous sodium chloride solution (5 ml)
  6. dry with materialThe solution was dried over anhydrous magnesium sulphate
  7. concentrationconcentrated
  8. customThe crude products were purified by column chromatography, silica
  9. washeluting with ethyl acetate in hexane (gradient 20% to 60% ethyl acetate)

Sources & evidence

ORD record
ord-9adcbf55847d44fa8fde7142eff630e5
Source dataset
uspto-grants-2010_04
Patent number
US07705027B2

Reaction notes

Loading…