Triphenylphosphine → 4-[2-(2-Cyclohexyl-5-methyl-oxazol-4-yl)-ethoxy]-3,5-dimethyl-benzaldehyde

HRID 2215208Notes

Reaction equation

HRID 2215208 reaction equation
[CH:1]1([C:7]2[O:8][C:9]([CH3:15])=[C:10]([CH2:12][CH2:13][OH:14])[N:11]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:16][C:17]1[CH:18]=[C:19]([CH:22]=[C:23]([CH3:26])[C:24]=1O)[CH:20]=[O:21].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1(C)C=CC=CC=1>[CH:1]1([C:7]2[O:8][C:9]([CH3:15])=[C:10]([CH2:12][CH2:13][O:14][C:24]3[C:23]([CH3:26])=[CH:22][C:19]([CH:20]=[O:21])=[CH:18][C:17]=3[CH3:16])[N:11]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 752223,5-Dimethyl-4-hydroxybenzaldehydeHCID 5363146Diisopropyl azodicarboxylateHCID 108567262-(2-Cyclohexyl-5-methyl-oxazol-4-yl)-ethanol

Product 1

HCID 219496594-[2-(2-Cyclohexyl-5-methyl-oxazol-4-yl)-ethoxy]-3,5-dimethyl-benzaldehyde

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

0.400 g of the above prepared 2-(2-cyclohexyl-5-methyl-oxazol-4-yl)-ethanol (1.91 mmol) was dissolved in 10 ml of toluene and treated successively at 0° C. with 0.287 g of 3,5-dimethyl-4-hydroxybenzaldehyde (1.91 mmol), 0.501 g of triphenylphosphine (1.91 mmol), and 0.387 g (1.91 mmol) of DIAD. The cooling bath was then removed and stirring continued for 2 h. Pouring onto crashed ice, twofold extraction with AcOEt, washing with dil. NaOH and water, drying over sodium sulfate, and evaporation of the solvents, followed by flash chromatography (SiO2, hexane/AcOEt=85/15) delivered finally 0.415 g of the title compound as colorless oil.

Workup

  1. customThe cooling bath was then removed
  2. additionPouring
  3. extractionice, twofold extraction with AcOEt
  4. washwashing with dil. NaOH and water
  5. dry with materialdrying over sodium sulfate, and evaporation of the solvents

Sources & evidence

ORD record
ord-db13957a9f79408bbd893d8d1d2589c1
Source dataset
uspto-grants-2006_09
Patent number
US07109225B2

Reaction notes

Loading…