Sulfuric Acid → HCID 57134471, compound
Reaction equation
[C:1]([S:4][CH:5]([CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:6][C:7]([OH:9])=[O:8])(=[O:3])[CH3:2].OS(O)(=O)=O>C(Cl)Cl>[C:12]([O:8][C:7](=[O:9])[CH2:6][CH:5]([S:4][C:1](=[O:3])[CH3:2])[CH2:10][CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)([CH3:17])([CH3:13])[CH3:11]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
3-Acetylsulfanyl-5-phenyl-pentanoic acid was taken up in DCM (15 mL) with stirring in a pressure bottle. c.H2SO4 (1 mL) was added and the solution cooled to −78° C. Isobutylene gas was bubbled through this solution until the volume had doubled. The pressure vessel was sealed and allowed to warm to room temperature and stirred overnight. The reaction was re-cooled to −78° C. and opened and warmed to room temparature. The excess isobuylene gas was allowed to evaporate and then the reaction solution was poured into a stirred 1 M Na2CO3 solution. The product was extracted into DCM and washed with brine, dried and filtered and evaporated under reduced pressure to give an orange oil (10.64 g, 34.5 mmol). 1H-NMR δ(CDCl3) 7.27-7.14 (5H, m), 3.88 (1H, m), 2.80-2.51 (4H, m), 2.34 (3H, s), 1.97-1.84 (2H, m) and 1.43 (9H, s).
Workup
- customIsobutylene gas was bubbled through this solution until the volume
- customThe pressure vessel was sealed
- temperatureto warm to room temperature
- stirringstirred overnight
- temperatureThe reaction was re-cooled to −78° C.
- temperaturewarmed to room temparature
- customto evaporate
- additionthe reaction solution was poured into a stirred 1 M Na2CO3 solution
- extractionThe product was extracted into DCM
- washwashed with brine
- customdried
- filtrationfiltered
- customevaporated under reduced pressure
Sources & evidence
- ORD record
- ord-6bc9cc78532047f1bb9ebc1320a705b0
- Source dataset
- uspto-grants-2002_11
- Patent number
- US06479502B1
Reaction notes
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