Ethyl Acetate → 1-(Hydroxy)-1-(4,5-diphenyloxazol-2-yl)-2-(3-methoxybenzyl)cyclooctane

HRID 1741381Notes

Reaction equation

HRID 1741381 reaction equation
[C:1]1([C:7]2[N:8]=[CH:9][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.C([Li])CCC.[CH3:23][O:24][C:25]1[CH:26]=[C:27]([CH:38]=[CH:39][CH:40]=1)[CH2:28][CH:29]1[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][C:30]1=[O:37].C(OCC)(=O)C>C1COCC1.O>[OH:37][C:30]1([C:9]2[O:10][C:11]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)=[C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[N:8]=2)[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH:29]1[CH2:28][C:27]1[CH:38]=[CH:39][CH:40]=[C:25]([O:24][CH3:23])[CH:26]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 6134984,5-DiphenyloxazoleHCID 183674112-(3-Methoxybenzyl)cyclooctanoneHCID 178418339Butyllithium

Product 1

HCID 183672891-(Hydroxy)-1-(4,5-diphenyloxazol-2-yl)-2-(3-methoxybenzyl)cyclooctaneYield 83.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 4,5-diphenyloxazole (2.1 g) in THF (30 ml) at -78° C. under N2 was added butyllithium (1.6M in hexane, 6.7 ml). After 30 minutes, a solution of 2-(3-methoxybenzyl)cyclooctanone (2.4 g) in THF (10 ml) was added thereto and stirred for 1 hour at the same temperature. The reaction mixture was poured into the mixture of ethyl acetate and water. The organic layer was washed with 1N-HCl solution, sat. NaHCO3, and brine, dried over MgSO4, and evaporated in vacuo. The residue was purified by chromatography on silica gel to afford 1-(hydroxy)-1-(4,5-diphenyloxazol-2-yl)-2-(3-methoxybenzyl)cyclooctane (3.7 g). MS (m/z): 468 (M+ +1) IR (Neat): 3400 cm-1NMR (CDCl3, δ): 1.2-2.0 (12H, m), 2.2-2.8 (3H, m), 3.38 (1H, s), 3.66 (3H, s), 6.5-6.8 (3H, m), 7.07 (1H, t, J=8 Hz), 7.3-7.8 (10H, m)

Workup

  1. washThe organic layer was washed with 1N-HCl solution, sat. NaHCO3, and brine
  2. dry with materialdried over MgSO4
  3. customevaporated in vacuo
  4. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-59c9f1a65a9b4a65892243be850f8921
Source dataset
uspto-grants-1999_10
Patent number
US05972965

Reaction notes

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