HCID 66609952, compound → 1-[(Methylsulfanyl)methyl]cyclopropane-1-carboxylic acid
Reaction equation
[CH3:1][S:2][CH2:3][C:4]1([C:7]([O:9]CC)=[O:8])[CH2:6][CH2:5]1>C(O)C.[OH-].[Na+]>[CH3:1][S:2][CH2:3][C:4]1([C:7]([OH:9])=[O:8])[CH2:6][CH2:5]1Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 23 °C
Procedure
A 50% solution of sodium hydroxide (12.63 mL, 243 mmol) was added to a stirred solution of ethyl 1-(methylthiomethyl)cyclopropanecarboxylate (5.43 g, 31.20 mmol) in absolute ethanol (62.30 mL) at 23° C. The resulting solution was stirred at 23° C. for 20 h. The reaction mixture was diluted with a 0.5 M solution of sodium hydroxide and washed with dichloromethane. The aqueous layer was acidified to pH≈1 with concentrated hydrochloric acid and extracted with dichloromethane. The combined organic layers were dried (Na2SO4), filtered, and concentrated and concentrated to dryness to give the desired product as a light brown oil (2.10 g, 46%): 1H NMR (300 MHz, CDCl3) δ 2.82 (s, 2H), 2.17 (s, 3H), 1.41 (dd, J=7, 4 Hz, 2H), 0.99 (dd, J=7, 4 Hz, 2H).
Workup
- washwashed with dichloromethane
- extractionextracted with dichloromethane
- dry with materialThe combined organic layers were dried (Na2SO4)
- filtrationfiltered
- concentrationconcentrated
- concentrationconcentrated to dryness
Sources & evidence
- ORD record
- ord-2a042c77ba044b60884f710d371829b3
- Source dataset
- uspto-grants-2014_08
- Patent number
- US08815271B2
Reaction notes
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