Cuminaldehyde → [Rac]-2-ethoxy-3-{4-[2-(4-isopropyl-phenyl)-5-methyl-oxazol-4-ylmethoxy]-5,6,7,8-tetrahydro-naphthalen-1-yl}-propionic acid ethyl ester

HRID 479179Notes

Reaction equation

HRID 479179 reaction equation
[H-].[Na+].[CH2:3]([O:5][C:6](=[O:23])[CH:7]([O:20][CH2:21][CH3:22])[CH2:8][C:9]1[C:18]2[CH2:17][CH2:16][CH2:15][CH2:14][C:13]=2[C:12]([OH:19])=[CH:11][CH:10]=1)[CH3:4].Cl[CH2:25][C:26]1[N:27]=[C:28]([C:32]2[CH:37]=[CH:36][C:35]([CH:38]([CH3:40])[CH3:39])=[CH:34][CH:33]=2)[O:29][C:30]=1[CH3:31].C(C1C=CC(C=O)=CC=1)(C)C.O=P(Cl)(Cl)Cl>CN(C)C=O.O>[CH2:3]([O:5][C:6](=[O:23])[CH:7]([O:20][CH2:21][CH3:22])[CH2:8][C:9]1[C:18]2[CH2:17][CH2:16][CH2:15][CH2:14][C:13]=2[C:12]([O:19][CH2:25][C:26]2[N:27]=[C:28]([C:32]3[CH:33]=[CH:34][C:35]([CH:38]([CH3:40])[CH3:39])=[CH:36][CH:37]=3)[O:29][C:30]=2[CH3:31])=[CH:11][CH:10]=1)[CH3:4]

Participants

8

Reactant 5

HCID 326CuminaldehydeHCID 24758Sodium hydrideHCID 24813Phosphorus oxychlorideHCID 219742554-(Chloromethyl)-2-(4-isopropylphenyl)-5-methyloxazoleHCID 69557425[Rac]-2-ethoxy-3-(4-hydroxy-5,6,7,8-tetrahydro-naphthalen-1-yl)-propionic acid ethyl ester

Product 1

HCID 69557022[Rac]-2-ethoxy-3-{4-[2-(4-isopropyl-phenyl)-5-methyl-oxazol-4-ylmethoxy]-5,6,7,8-tetrahydro-naphthalen-1-yl}-propionic acid ethyl esterYield 67.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

0.037 g (1.54 mmol) Sodium hydride was added in small portions below 30° C. and under argon to a solution of 0.30 g (1.03 mmol) [rac]-2-ethoxy-3-(4-hydroxy-5,6,7,8-tetrahydro-naphthalen-1-yl)-propionic acid ethyl ester in 5.0 ml N,N-dimethylformamide. After 10 minutes, 0.384 g (1.54 mmol) 4-chloromethyl-2-(4-isopropyl-phenyl)-5-methyl-oxazole (prepared from 4-isopropyl-benzaldehyde and diacetyl monoxyme followed by treatment with POCl3 in analogy to the procedures described in examples 21 a] and b]) were added and the reaction mixture then stirred for 16 hours at ambient temperature. It was then diluted with water and extracted with ether. The combined organic phases were dried over MgSO4 and evaporated. The residue formed was purified by flash-chromatography (silica gel; eluent: gradient of hexane and ethyl acetate) to give 0.35 g (67%) of [rac]-2-ethoxy-3-{4-[2-(4-isopropyl-phenyl)-5-methyl-oxazol-4-ylmethoxy]-5,6,7,8-tetrahydro-naphthalen-1-yl}-propionic acid ethyl ester as colorless oil.

Workup

  1. additionwere added
  2. extractionextracted with ether
  3. dry with materialThe combined organic phases were dried over MgSO4
  4. customevaporated
  5. customThe residue formed
  6. customwas purified by flash-chromatography (silica gel; eluent: gradient of hexane and ethyl acetate)

Sources & evidence

ORD record
ord-aab6d2ce9a0746aa989c9f03e29c7046
Source dataset
uspto-grants-2003_11
Patent number
US06642389B2

Reaction notes

Loading…