4-Toluenesulfonyl chloride → HCID 131712415, compound
Reaction equation
[Cl:1][CH:2]([Cl:15])[CH:3]([C@H:5]1[C@H:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:6]1([CH3:14])[CH3:13])[OH:4].[S:16](Cl)([C:19]1[CH:25]=[CH:24][C:22]([CH3:23])=[CH:21][CH:20]=1)(=[O:18])=[O:17]>N1C=CC=CC=1>[CH2:11]([O:10][C:8]([C@H:7]1[C@H:5]([CH:3]([O:4][S:16]([C:19]2[CH:25]=[CH:24][C:22]([CH3:23])=[CH:21][CH:20]=2)(=[O:18])=[O:17])[CH:2]([Cl:15])[Cl:1])[C:6]1([CH3:14])[CH3:13])=[O:9])[CH3:12]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 40 °C
Procedure
A solution of (±) trans ethyl 3-(β,β-dichloro-α-hydroxyethyl)-2,2-dimethylcyclopropane-1-carboxylate (28.0 g, 0.11 M) in pyridine (168 ml) was added dropwise to a solution of tosyl chloride (44.2 g, 0.23 M) in pyridine (224 ml) maintained at 40° C. After the addition the mixture was stored for 3 days at 4° C. The majority of the pyridine was removed under vacuum at 40° C. and the residue was poured into ice/water (200 ml). After acidification with concentrated hydrochloric acid, this mixture was extracted with ether (3×100 ml), the ether layers combined, dried and evaporated to a pale yellow oil, which crystallised on standing. The tosylate was recrystallised from cyclohexane, m.p. 71° C.
Workup
- additionAfter the addition the mixture
- customThe majority of the pyridine was removed under vacuum at 40° C.
- additionthe residue was poured into ice/water (200 ml)
- extractionAfter acidification with concentrated hydrochloric acid, this mixture was extracted with ether (3×100 ml)
- customdried
- customevaporated to a pale yellow oil, which
- customcrystallised
- customThe tosylate was recrystallised from cyclohexane, m.p. 71° C.
Sources & evidence
- ORD record
- ord-dc93d47619274064820c057ffd28389f
- Source dataset
- uspto-grants-1981_09
- Patent number
- US04289711
Reaction notes
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