2,4-Dihydroxybenzaldehyde → 2-Hydroxy-4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-benzaldehyde

HRID 1394746Notes

Reaction equation

HRID 1394746 reaction equation
[OH:1][C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:30]1([C:36]2[O:37][C:38]([CH3:44])=[C:39]([CH2:41][CH2:42]O)[N:40]=2)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O>C1COCC1>[OH:1][C:2]1[CH:9]=[C:8]([O:10][CH2:42][CH2:41][C:39]2[N:40]=[C:36]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[O:37][C:38]=2[CH3:44])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5]

Participants

6

Reactant 4

HCID 72132,4-DihydroxybenzaldehydeHCID 11776TriphenylphosphineHCID 97268Di-tert-butyl azodicarboxylateHCID 7255852-(5-Methyl-2-phenyl-4-oxazolyl)ethanol

Product 1

HCID 222739232-Hydroxy-4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-benzaldehydeYield 48.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2,4-dihydroxy-benzaldehyde (2 g, 14.5 mmol) in 20 ml THF was cooled to 0° C. To this solution were added triphenylphosphine (9.7 g, 37 mmol), 2-(2-phenyl-5-methyl-oxazol-4-yl)-ethanol (2.84 g, 14 mmol) and finally during 0.75 hours a solution of di-tert-butyl azodicarboxylate (8.52 g, 37 mmol) in 20 ml THF. The reaction mixture was stirred overnight at room temperature, evaporated to dryness, purified by chromatography (SiO2; AcOEt/heptane) and the product was crystallized from AcOEt/ether/heptane to yield 2.2 g (46%) of the title compound as a colorless solid.

Workup

  1. customevaporated to dryness
  2. custompurified by chromatography (SiO2; AcOEt/heptane)
  3. customthe product was crystallized from AcOEt/ether/heptane

Sources & evidence

ORD record
ord-8de5f5f4c7834f75abe634c362c3840a
Source dataset
uspto-grants-2008_03
Patent number
US07348349B2

Reaction notes

Loading…