Triethylamine → Benzenesulfonic acid, 3-nitro-, (2S)-2-oxiranylmethyl ester
Reaction equation
C(N(CC)CC)C.[CH2:8]1[O:10][C@@H:9]1[CH2:11][OH:12].[N+:13]([C:16]1[CH:17]=[C:18]([S:22](Cl)(=[O:24])=[O:23])[CH:19]=[CH:20][CH:21]=1)([O-:15])=[O:14].C1OC1CO>ClCCl>[CH2:8]1[O:10][C@@H:9]1[CH2:11][O:12][S:22]([C:18]1[CH:17]=[C:16]([N+:13]([O-:15])=[O:14])[CH:21]=[CH:20][CH:19]=1)(=[O:23])=[O:24]Participants
Conditions
- Temperature
- 0 °C
Procedure
A 250 ml rounded bottom flask was charged with triethylamine (3.3 g, 4.5 ml, 32 mmol), R-glycidol (2.0 g, 27 mmol)(Arco Company, Newton Square, PA) and dichloromethane (50 ml) then cooled to 0° C. A solution of 3-nitrobenzenesulfonyl chloride (6.0 g, 27 mmol) in dichloromethane (40 ml) was added dropwise over a 5-minute period to the glycidol solution and the reaction mixture was stirred at 0° C. under N2 for 3 hrs. The reaction mixture was poured into a separatory funnel and washed successively with 1N aqueous hydrochloric acid (90 ml), 5% aqueous sodium bicarbonate solution (90 ml), and saturated aqueous sodium chloride. The organic layer was separated, dried over anhydrous magnesium sulfate (10 g), filtered and concentrated in vacuo to yield (2S)-(+)-glycidyl-3-nitrobenzenesulfonate as a pale colored solid. Recrystallization from hexanes/EtOAc (1:1, 50 ml) provided 5.89 g (83%) of pure (2S)-(+)-glycidyl- 3-nitrobenzenesulfonate, m.p. 61°-63° C., [α]D +22.3° (c 0.41, chloroform), >95% optical purity.
Workup
- additionThe reaction mixture was poured into a separatory funnel
- washwashed successively with 1N aqueous hydrochloric acid (90 ml), 5% aqueous sodium bicarbonate solution (90 ml), and saturated aqueous sodium chloride
- customThe organic layer was separated
- dry with materialdried over anhydrous magnesium sulfate (10 g)
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-66900017dd154dfa9e3ed7dcf6ff1c71
- Source dataset
- uspto-grants-1991_10
- Patent number
- US05053338
Reaction notes
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