Sodium hydride → HCID 59557738, compound
Reaction equation
[CH:1]1([OH:5])[CH2:4][CH2:3][CH2:2]1.[H-].[Na+].CC1C=CC(S(O[CH2:19][CH2:20][O:21][C:22]2[CH:27]=[CH:26][C:25]([CH2:28][C:29]3[CH:34]=[C:33]([Br:35])[CH:32]=[CH:31][C:30]=3[Cl:36])=[CH:24][CH:23]=2)(=O)=O)=CC=1>O1CCCC1>[Br:35][C:33]1[CH:32]=[CH:31][C:30]([Cl:36])=[C:29]([CH2:28][C:25]2[CH:26]=[CH:27][C:22]([O:21][CH2:20][CH2:19][O:5][CH:1]3[CH2:4][CH2:3][CH2:2]3)=[CH:23][CH:24]=2)[CH:34]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of cyclobutanol (260 mg, 3.6 mmol) in anhydrous tetrahydrofuran (4 mL) was added sodium hydride (138 mg, 5.7 mmol) in portions at 0° C. The mixture was stirred at 0° C. for 30 min, and then 2-(4-(5-bromo-2-chlorobenzyl)phenoxy)ethyl 4-methylbenzenesulfonate (intermediate AB) (300 mg, 0.6 mmol) was added in portions. The mixture was refluxed for 3 h, whereupon TLC showed the reaction was complete. The reaction mixture was quenched with saturated ammonium chloride, extracted with ethyl acetate, washed with water and then with brine, dried over anhydrous sodium sulfate, and concentrated to a crude oil. The crude oil was purified by column chromatography (PE:EA=10:1) to get intermediate CL as an oil product (117 mg, yield: ˜49%).
Workup
- temperatureThe mixture was refluxed for 3 h, whereupon TLC
- customThe reaction mixture was quenched with saturated ammonium chloride
- extractionextracted with ethyl acetate
- washwashed with water
- dry with materialwith brine, dried over anhydrous sodium sulfate
- concentrationconcentrated to a crude oil
- customThe crude oil was purified by column chromatography (PE:EA=10:1)
Sources & evidence
- ORD record
- ord-865e0d513a33441ba1d021aa0d53b28c
- Source dataset
- uspto-grants-2014_08
- Patent number
- US08802637B2
Reaction notes
Loading…