Isopropanol → HCID 57443322, compound

HRID 2261799Notes

Reaction equation

HRID 2261799 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[CH:6][C:5]=1[OH:11].[C:13]1(P(C2C=CC=CC=2)C2C=CC=CC=2)[CH:18]=CC=C[CH:14]=1.C(O)(C)C.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[CH:6][C:5]=1[O:11][CH:13]([CH3:18])[CH3:14]

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 11776TriphenylphosphineHCID 78400Benzoic acid, 2-hydroxy-4-methyl-, methyl esterHCID 5363146Diisopropyl azodicarboxylate

Product 1

HCID 57443322HCID 57443322, compoundYield 112%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 2-hydroxy-4-methyl-benzoic acid methyl ester (1.0 g, 6.0 mmol), triphenylphosphine (1.9 g, 7.2 mmol), and isopropanol (0.72 g, 12.0 mmol) in THF (10.0 mL) is added DIAD (1.45 g, 7.2 mmol) dropwise at 0° C. The mixture is stirred at room temperature overnight. The mixture is evaporated to dryness under reduced pressure. The residue is partitioned between EtOAc (50 mL) and water (50 mL). The organic phase is washed with brine (50 mL), dried (Na2SO4), filtered, and concentrated under reduced pressure to a residue. The residue is purified by flash chromatography to afford the title compound as white solid (1.4 g, 96%). LC-ES/MS m/e 209.0 (M+1).

Workup

  1. customThe mixture is evaporated to dryness under reduced pressure
  2. customThe residue is partitioned between EtOAc (50 mL) and water (50 mL)
  3. washThe organic phase is washed with brine (50 mL)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure to a residue
  7. customThe residue is purified by flash chromatography

Sources & evidence

ORD record
ord-d4bbc817588f42bb860782242a46bdc3
Source dataset
uspto-grants-2010_12
Patent number
US07846960B2

Reaction notes

Loading…