[2-(4-Bromo-phenyl)4-isopropyl-oxazol-5-yl]-methanol → 2-(4-Bromo-phenyl)4-isopropyl-oxazole-5-carbaldehyde

HRID 860592Notes

Reaction equation

HRID 860592 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]([CH2:16][OH:17])=[C:11]([CH:13]([CH3:15])[CH3:14])[N:12]=2)=[CH:4][CH:3]=1>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[O:9][C:10]([CH:16]=[O:17])=[C:11]([CH:13]([CH3:15])[CH3:14])[N:12]=2)=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 69056838[2-(4-Bromo-phenyl)4-isopropyl-oxazol-5-yl]-methanol

Product 1

HCID 858606262-(4-Bromo-phenyl)4-isopropyl-oxazole-5-carbaldehydeYield 81.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of [2-(4-bromo-phenyl)-4-isopropyl-oxazol-5-yl]-methanol (17.9 g, 60.4 mmol) in CH2Cl2 (450 mL) is treated at ambient temperature with acetic acid 1,1-diacetoxy-3-oxo-1·5-ioda-2-oxa-indan-1-yl ester (39 g, 92 mmol, Dess Martin reagent). The suspension is stirred 1 h and is partitioned between 10% aqueous Na2S2O3 solution (250 mL) and CH2Cl2 (150 mL). The organic layer is washed with saturated NaHCO3 (2×250 mL), and the combined aqueous layers are back-extracted with Et2O (300 mL). The combined organic layers are dried (Na2SO4) and concentrated. The crude product is purified by silica gel flash chromatography using hexanes:ethyl acetate (6:1) to give an offwhite solid (14.4 g, 81%).

Workup

  1. customis partitioned between 10% aqueous Na2S2O3 solution (250 mL) and CH2Cl2 (150 mL)
  2. washThe organic layer is washed with saturated NaHCO3 (2×250 mL)
  3. extractionthe combined aqueous layers are back-extracted with Et2O (300 mL)
  4. dry with materialThe combined organic layers are dried (Na2SO4)
  5. concentrationconcentrated
  6. customThe crude product is purified by silica gel flash chromatography

Sources & evidence

ORD record
ord-9db31e5d622f4ebe8be66da549a9f2e4
Source dataset
uspto-grants-2006_12
Patent number
US07153878B2

Reaction notes

Loading…