Isopropanol → HCID 57443322, compound

HRID 2261846Notes

Reaction equation

HRID 2261846 reaction equation
N(C([O-])=O)=NC([O-])=O.[OH:9][C:10]1[CH:19]=[C:18]([CH3:20])[CH:17]=[CH:16][C:11]=1[C:12]([O:14][CH3:15])=[O:13].[CH:21](O)([CH3:23])[CH3:22].C1COCC1>C(OCC)(=O)C.O>[CH3:15][O:14][C:12](=[O:13])[C:11]1[CH:16]=[CH:17][C:18]([CH3:20])=[CH:19][C:10]=1[O:9][CH:21]([CH3:23])[CH3:22]

Participants

7

Reactant 4

HCID 3776IsopropanolHCID 8028TetrahydrofuranHCID 78400Benzoic acid, 2-hydroxy-4-methyl-, methyl esterHCID 51573101N-carboxylatoiminocarbamate

Product 1

HCID 57443322HCID 57443322, compoundYield 81.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Disopropyl azodicarboxylate (8.7 mL, 44 mmol) is added to a stirred solution of methyl 2-hydroxy-4-methylbenzoate (4.85 g, 29.2 mmol), isopropanol (3.3 mL, 44 mmol), triphenylphosphene (11.5 g, 43.8 mmol) and THF (50 mL) at room temperature. The exothermic reaction is cooled in an ice bath and is allowed to stir overnight at room temperature. The mixture is diluted with ethyl acetate and water, and the organic phase is washed with brine and dried over MgSO4. The crude residue is purified by flash chromatography (20 to 40% EtOAc/heptane) to afford the title compound (4.95 g, 81%) as an oil. ES/MS m/e 209.3 (M+1).

Workup

  1. customThe exothermic reaction
  2. temperatureis cooled in an ice bath
  3. washthe organic phase is washed with brine
  4. dry with materialdried over MgSO4
  5. customThe crude residue is purified by flash chromatography (20 to 40% EtOAc/heptane)

Sources & evidence

ORD record
ord-a8d9588ef48743f6b756d00124de4ef2
Source dataset
uspto-grants-2010_12
Patent number
US07846960B2

Reaction notes

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