Iodoethane → 3-Ethyl-3-(3-methoxyphenyl)azepan-2-one
Reaction equation
[Li][CH2:2][CH2:3][CH2:4][CH3:5].CCCCCC.CC1(C)CCCC(C)(C)N1.C[Si](C)(C)[N:24]1[CH2:30][CH2:29][CH2:28][CH2:27]C[C:25]1=[O:31].Cl[C:35]1[CH:40]=[CH:39]C=[CH:37][C:36]=1[O:41][CH3:42].C(I)C>C1COCC1>[CH2:4]([C:3]1([C:2]2[CH:39]=[CH:40][CH:35]=[C:36]([O:41][CH3:42])[CH:37]=2)[CH2:27][CH2:28][CH2:29][CH2:30][NH:24][C:25]1=[O:31])[CH3:5]Participants
Reactant 6
Product 1
Reagents, catalysts & solvents 1
Procedure
To 1.6 M n-BuLi in hexane (31.3 mL, 50 mmol) at 0° C. was added a solution of 2,2,6,6-tetramethyl piperidine (8.43 mL, 50 mmol) in anhydrous THF (100 mL) over 5 min. 1-Trimethylsilanyl-azepan-2-one (as described in Step F above) (9.26 g, 50 mmol) in anhydrous THF (20 mL) was added. After stirring the reaction mixture for 10 min, a further portion of 1.6M n-BuLi in hexane (31.3 mL, 50 mmol) was added, the mixture stirred for 10 min, and 2-chloroanisole (6.34 mL, 50 mmol) was added. After stirring for 30 min under Ar, ethyl iodide (3.90 mL, 48.7 mmol) was added, the reaction mixture was stirred for 30 min, quenched with H2O, concentrated in vacuo, diluted with EtOAc, and washed with 5N HCl (100 mL) and brine. The organic layer was dried (MgSO4), concentrated and purified using SiO2 chromatography (10-15% EtOAc/CH2Cl2) to give the title compound
Workup
- stirringthe mixture stirred for 10 min
- additionwas added
- stirringthe reaction mixture was stirred for 30 min
- customquenched with H2O
- concentrationconcentrated in vacuo
- additiondiluted with EtOAc
- washwashed with 5N HCl (100 mL) and brine
- dry with materialThe organic layer was dried (MgSO4)
- concentrationconcentrated
- custompurified
Sources & evidence
- ORD record
- ord-382a25474c234a80afc519e85113c9d9
- Source dataset
- uspto-grants-2001_11
- Patent number
- US06316436B1
Reaction notes
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