Ethyl Acetate → ethyl (R)-{3-{[2-(4,5-diphenyloxazole-2-yl)-1-hydroxy-2-cyclohexen-1-yl]methyl}phenoxy}-acetate

HRID 379319Notes

Reaction equation

HRID 379319 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([C:18]3[C@:19]([O:49][Si](C)(C)C)([CH2:24][C:25]4[CH:30]=[CH:29][CH:28]=[C:27]([O:31][Si](C(C)(C)C)(C5C=CC=CC=5)C5C=CC=CC=5)[CH:26]=4)[CH2:20][CH2:21][CH2:22][CH:23]=3)[O:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[CH3:72][CH2:73][O:74][C:75]([CH3:77])=[O:76]>C1COCC1>[C:1]1([C:7]2[N:8]=[C:9]([C:18]3[C@@:19]([CH2:24][C:25]4[CH:26]=[C:27]([CH:28]=[CH:29][CH:30]=4)[O:31][CH2:77][C:75]([O:74][CH2:73][CH3:72])=[O:76])([OH:49])[CH2:20][CH2:21][CH2:22][CH:23]=3)[O:10][C:11]=2[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 2724141Tetrabutylammonium FluorideHCID 15550206(R)-2-(4,5-diphenyloxazol-2-yl)-1-trimethylsilyloxy-1-[3-(tertbutyldiphenylsiloxy)benzyl]-2-cyclohexene

Product 1

HCID 15550207ethyl (R)-{3-{[2-(4,5-diphenyloxazole-2-yl)-1-hydroxy-2-cyclohexen-1-yl]methyl}phenoxy}-acetate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (R)-2-(4,5-diphenyloxazol-2-yl)-1-trimethylsilyloxy-1-[3-(tertbutyldiphenylsiloxy)benzyl]-2-cyclohexene (10 g) in THF (50 ml) was added tetrabutylammonium fluoride (41 ml, 1M solution in THF) at room temperature. After being stirred for 4 hours, the mixture was diluted with EtOAc. The mixture was washed with 1N-HCl solution and brine and evaporated. The residue was dissolved in DMF (50 ml), followed by addition of K2CO3 (5 g) and ethyl bromoacetate (2.0 ml) at room temperature. The mixture was stirred for 2 hours at the same temperature and partitioned between EtOAc and water. The organic layer was washed with water and brine and evaporated in vacuo. The residue was purified by chromatography on silica gel to give ethyl (R)-{3-{[2-(4,5-diphenyloxazole-2-yl)-1-hydroxy-2-cyclohexen-1-yl]methyl}phenoxy}-acetate (5.3 g).

Workup

  1. washThe mixture was washed with 1N-HCl solution and brine
  2. customevaporated
  3. dissolutionThe residue was dissolved in DMF (50 ml)
  4. additionfollowed by addition of K2CO3 (5 g) and ethyl bromoacetate (2.0 ml) at room temperature
  5. stirringThe mixture was stirred for 2 hours at the same temperature
  6. custompartitioned between EtOAc and water
  7. washThe organic layer was washed with water and brine
  8. customevaporated in vacuo
  9. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-bf2eb6408ae7429d83bed8b74b6077d7
Source dataset
uspto-grants-2001_10
Patent number
US06297267B1

Reaction notes

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