Triethylamine → [(E)-(6-methoxy-2,3-dihydroinden-1-ylidene)amino] methanesulfonate
Reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][CH2:8]/[C:9]/2=[N:12]\[OH:13])=[CH:5][CH:4]=1.CCN(CC)CC.[CH3:21][S:22](Cl)(=[O:24])=[O:23]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH3:21][S:22]([O:13]/[N:12]=[C:9]1\[CH2:8][CH2:7][C:6]2[C:10]\1=[CH:11][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)(=[O:24])=[O:23]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
To the solution of intermediate 16 (6.6 g, 37.2 mmol) in CH2Cl2 (120 mL) was added Et3N (20.6 mL, 149 mmol), DMAP (455 mg, 3.73 mmol) and MsCl (4.35 mL, 55.87 mmol). The mixture was stirred at rt overnight. The reaction mixture was washed successively with water, saturated aq NH4Cl, brine, dried over anhydrous MgSO4, filtered and concentrated. The crude product was purified by flash chromatography on silica gel column (elution with PE/CH2Cl2=1:1) to give (E)-6-methoxy-2,3-dihydro-1H-inden-1-one O-methylsulfonyl oxime (intermediate 17) (736 g, 82%) as a white solid.
Workup
- washThe reaction mixture was washed successively with water, saturated aq NH4Cl, brine
- dry with materialdried over anhydrous MgSO4
- filtrationfiltered
- concentrationconcentrated
- customThe crude product was purified by flash chromatography on silica gel column (elution with PE/CH2Cl2=1:1)
Sources & evidence
- ORD record
- ord-fccb115ae67b4acbbabfe096266fff67
- Source dataset
- uspto-grants-2015_10
- Patent number
- US09156822B2
Reaction notes
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