Iodoethane → N-(7-ethoxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-2,2,2-trifluoro-N-propyl-acetamide
Reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]([N:5]([CH:9]1[CH2:18][CH2:17][C:16]2[C:11](=[CH:12][C:13]([OH:19])=[CH:14][CH:15]=2)[CH2:10]1)[CH2:6][CH2:7][CH3:8])=[O:4].[CH3:22][C:23](C)([O-])C.[K+].C(I)C>CS(C)=O>[CH2:22]([O:19][C:13]1[CH:12]=[C:11]2[C:16]([CH2:17][CH2:18][CH:9]([N:5]([CH2:6][CH2:7][CH3:8])[C:3](=[O:4])[C:2]([F:20])([F:21])[F:1])[CH2:10]2)=[CH:15][CH:14]=1)[CH3:23]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 2,2,2-trifluoro-N-(7-hydroxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-N-propyl-acetamide (1.0 g, 3.32 mmol) in DMSO (30 mL) under an inert atmosphere was added a slurry of potassium t-butoxide (392 mg, 3.49 mmol, 1.05 eq.) in DMSO (10 mL). The reaction was stirred at room temperature for 30 min. and then ethyl iodide (0.32 mL, 3.98 mmol, 1.2 eq.) was added dropwise. The reaction mixture was stirred for 2 h, quenched with water, and extracted with EtOAc (2×50 mL). The combined organic layers were dried over MgSO4, filtered, and concentrated onto silica gel (10 g). This was placed on top of a flash column and eluted with 20% acetone in hexanes to afford N-(7-ethoxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-2,2,2-trifluoro-N-propyl-acetamide as an oil (660 mg).
Workup
- stirringThe reaction mixture was stirred for 2 h
- customquenched with water
- extractionextracted with EtOAc (2×50 mL)
- dry with materialThe combined organic layers were dried over MgSO4
- filtrationfiltered
- concentrationconcentrated onto silica gel (10 g)
- washeluted with 20% acetone in hexanes
Sources & evidence
- ORD record
- ord-11e51fdc516e4f26b3a90907f11531ad
- Source dataset
- uspto-grants-2003_09
- Patent number
- US06627644B2
Reaction notes
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