Hydrochloric Acid → 3-Hydroxyvalerate thiophenyl ester
Reaction equation
C[Al](C)C.[C:5]1([SH:11])[CH:10]=[CH:9][CH:8]=CC=1.[OH:12][CH:13]([CH2:18][CH3:19])[CH2:14][C:15]([O-:17])=[O:16].Cl>ClCCl>[S:11]1[CH:8]=[CH:9][CH:10]=[C:5]1[O:17][C:15](=[O:16])[CH2:14][CH:13]([OH:12])[CH2:18][CH3:19]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
In a dry flask on ice, 3 ml of dehydrated dichloromethane was stirred and 1 ml of 2M trimethyl aluminum was slowly added thereto under a nitrogen stream. After that, 1 mmol of thiophenol was slowly added thereto. The mixture was stirred at room temperature for 30 minutes and then 3-hydroxyvalerate dissolved in 3 ml of dehydrated dichloromethane was added thereto. The reaction was monitored by a TLC. To this mixed solution was added 10 ml of dichloromethane and, until generation of bubbles stopped, 10 ml of 3% hydrochloric acid solution was added. The mixed solution was transferred to a separating funnel, washed with 3% hydrochloric acid solution for two times and with saturated saline for two times, dried over magnesium sulfate and evaporated in vacuo to give 258 mg of crude oily 3-hydroxyvalerate thiophenyl ester in dark yellow color. This was purified by a column chromatography (20 cm×1 cm diameter; eluent was hexane:ethyl acetate=2:1) using silica gel 60 to give 44 mg of pure 3-hydroxyvalerate thiophenyl ester as a transparent oil. The yield to the unpurified substance was 17%. Result of NMR analysis of this compound is as follows.
Workup
- additionwas added
- customThe mixed solution was transferred to a separating funnel
- washwashed with 3% hydrochloric acid solution for two times and with saturated saline for two times
- dry with materialdried over magnesium sulfate
- customevaporated in vacuo
Sources & evidence
- ORD record
- ord-f60ade4a3e624b67aac66e6cf029dd81
- Source dataset
- uspto-grants-2011_05
- Patent number
- US07943351B2
Reaction notes
Loading…