Cyclopentanol → HCID 59557760, compound
Reaction equation
[CH:1]1([OH:6])[CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].CC1C=CC(S(O[CH2:20][CH2:21][O:22][C:23]2[CH:28]=[CH:27][C:26]([CH2:29][C:30]3[CH:35]=[C:34]([Br:36])[CH:33]=[CH:32][C:31]=3[Cl:37])=[CH:25][CH:24]=2)(=O)=O)=CC=1>C1COCC1>[Br:36][C:34]1[CH:33]=[CH:32][C:31]([Cl:37])=[C:30]([CH2:29][C:26]2[CH:27]=[CH:28][C:23]([O:22][CH2:21][CH2:20][O:6][CH:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)=[CH:24][CH:25]=2)[CH:35]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of cyclopentanol (0.86 g) in anhydrous THF (8.6 mL), NaH (2.0 eq) was added in portions at 0° C., and then the mixture was stirred at 0° C. for 3 h. Then 2-(4-(5-bromo-2-chlorobenzyl)phenoxy)ethyl 4-methylbenzenesulfonate (intermediate AB) (2.43 g, 0.5 eq) was added in portions. The mixture was stirred at room temperature overnight, whereupon TLC showed the reaction was complete. Then the reaction mixture was quenched with saturated NH4Cl, extracted with EtOAc, washed with water and brine, dried with anhydrous Na2SO4, and concentrated to a crude oil. The crude oil was purified by column chromatography (PE:EA=100:1) to obtain oil AC (1.0 g, yield ˜50%).
Workup
- stirringThe mixture was stirred at room temperature overnight, whereupon TLC
- customThen the reaction mixture was quenched with saturated NH4Cl
- extractionextracted with EtOAc
- washwashed with water and brine
- dry with materialdried with anhydrous Na2SO4
- concentrationconcentrated to a crude oil
- customThe crude oil was purified by column chromatography (PE:EA=100:1)
- customto obtain oil AC (1.0 g, yield ˜50%)
Sources & evidence
- ORD record
- ord-597c2339d04f413c8a8e2da7389b414e
- Source dataset
- uspto-grants-2014_08
- Patent number
- US08802637B2
Reaction notes
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