Methylparaben → Methyl 4-[(5-bromo-2-cyclopropyl-1,3-oxazol-4-yl)methoxy]benzoate

HRID 1519251Notes

Reaction equation

HRID 1519251 reaction equation
[Br:1][C:2]1[O:6][C:5]([CH:7]2[CH2:9][CH2:8]2)=[N:4][C:3]=1[CH2:10][OH:11].[C:12]([C:16]1[CH:21]=[CH:20][C:19](O)=[CH:18][CH:17]=1)([O:14][CH3:15])=[O:13].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[Br:1][C:2]1[O:6][C:5]([CH:7]2[CH2:8][CH2:9]2)=[N:4][C:3]=1[CH2:10][O:11][C:19]1[CH:20]=[CH:21][C:16]([C:12]([O:14][CH3:15])=[O:13])=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 7456MethylparabenHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 67460559(5-Bromo-2-cyclopropyl-1,3-oxazol-4-yl)methanol2×

Product 1

HCID 67460431Methyl 4-[(5-bromo-2-cyclopropyl-1,3-oxazol-4-yl)methoxy]benzoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (5-bromo-2-cyclopropyl-1,3-oxazol-4-yl)methanol (intermediate D3.1, 0.10 g, 0.46 mmol) in THF (4 ml) was added 4-carbomethoxyphenol (0.11 g, 0.69 mmol), Ph3P (0.18 g, 0.69 mmol) and DIAD (0.13 ml, 0.69 mmol). After 2 h at rt, the reaction was concentrated and purified by flash chromatography (silica, 0-35% EtOAc/hexanes) to give methyl 4-[(5-bromo-2-cyclopropyl-1,3-oxazol-4-yl)methoxy]benzoate. LCMS [M+H]+=352.2.

Workup

  1. concentrationthe reaction was concentrated
  2. custompurified by flash chromatography (silica, 0-35% EtOAc/hexanes)

Sources & evidence

ORD record
ord-10f4eb317fbe4c9f945c82cc78d920e0
Source dataset
uspto-grants-2015_07
Patent number
US09073879B2

Reaction notes

Loading…