Lithium Hydroxide → HCID 21051842, compound
Reaction equation
C[O:2][C:3](=[O:19])[CH:4]([C:11]1[CH:16]=[CH:15][C:14]([S:17][CH3:18])=[CH:13][CH:12]=1)[CH2:5][C@H:6]1[CH2:10][CH2:9][CH2:8][O:7]1.[OH-].[Li+]>CO>[CH3:18][S:17][C:14]1[CH:13]=[CH:12][C:11]([CH:4]([CH2:5][C@H:6]2[CH2:10][CH2:9][CH2:8][O:7]2)[C:3]([OH:19])=[O:2])=[CH:16][CH:15]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
A solution of 2-(4-methylsulfanyl-phenyl)-3-(tetrahydro-furan-2(R)-yl)-propionic acid methyl ester (0.693 g, 2.47 mmol) in methanol (10 mL) was treated with a 0.8M aqueous lithium hydroxide solution (4.01 mL, 4.94 mmol). The reaction mixture was stirred at 25° C. for 16 h and then was concentrated in vacuo to remove methanol. The remaining aqueous layer was acidified to pH=2 with a 10% aqueous hydrochloric acid solution and then was extracted with ethyl acetate (2×10 mL). The combined organic layers were washed with a saturated aqueous sodium chloride solution (1×10 mL), dried over sodium sulfate, filtered, and concentrated in vacuo to afford pure 2-(4-methylsulfanyl-phenyl)-3-(tetrahydro-furan-2(R)-yl)-propionic acid (0.653 g, 99%) as a light yellow oil that crystallized upon standing: mp 105-107° C.; [α]23589=−14.93° (c=0.75, chloroform); EI-HRMS m/e calcd for C14H18O3S (M+) 266.0976. found 266.0976.
Workup
- concentrationwas concentrated in vacuo
- customto remove methanol
- extractionwas extracted with ethyl acetate (2×10 mL)
- washThe combined organic layers were washed with a saturated aqueous sodium chloride solution (1×10 mL)
- dry with materialdried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-3510b7f4e2384547968be92593579e37
- Source dataset
- uspto-grants-2007_08
- Patent number
- US07259166B2
Reaction notes
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