p-Toluenesulfonic acid → HCID 18680097, compound
Reaction equation
O[CH:2]([C:7]1[CH:8]=[C:9]([CH:19]2[CH2:21][CH:20]2[C:22]2[CH:31]=[C:30]3[C:25]([CH2:26][CH2:27][N:28]=[C:29]3[CH:32]([CH3:34])[CH3:33])=[CH:24][CH:23]=2)[CH:10]=[C:11]2[C:16]=1[CH:15]=[C:14]([C:17]#[N:18])[CH:13]=[CH:12]2)[CH2:3][CH:4]([CH3:6])[CH3:5].C1(C)C=CC(S(O)(=O)=O)=CC=1>C(OCCOCC)C>[CH:32]([C:29]1[C:30]2[C:25](=[CH:24][CH:23]=[C:22]([CH:20]3[CH2:21][CH:19]3[C:9]3[CH:10]=[C:11]4[C:16](=[C:7](/[CH:2]=[CH:3]/[CH:4]([CH3:6])[CH3:5])[CH:8]=3)[CH:15]=[C:14]([C:17]#[N:18])[CH:13]=[CH:12]4)[CH:31]=2)[CH2:26][CH2:27][N:28]=1)([CH3:34])[CH3:33]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 185 °C
Procedure
A solution of Example 8G (120 mg, 0.27 mmol) in 1,2 diethoxyethane was treated with para-toluenesulfonic acid (253 mg, 1.3 mmol) and 3 Å molecular sieves (500 mg), heated to 185° C., and stirred for 3 hours. The mixture was cooled to room temperature, quenched with saturated NaHCO3, and extracted with ethyl acetate. The combined extracts were washed with water, dried (Na2SO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 25% ethyl acetate/hexanes to provide the desired product.
Workup
- temperatureThe mixture was cooled to room temperature
- customquenched with saturated NaHCO3
- extractionextracted with ethyl acetate
- washThe combined extracts were washed with water
- dry with materialdried (Na2SO4)
- filtrationfiltered
- concentrationconcentrated
- customThe concentrate was purified by flash column chromatography on silica gel with 25% ethyl acetate/hexanes
Sources & evidence
- ORD record
- ord-61f171d02a9e410eaed3c786896bd71d
- Source dataset
- uspto-grants-2002_12
- Patent number
- US06495562B1
Reaction notes
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