Acetyl chloride → 3-Acetoxycyclobutanecarboxylic acid
Reaction equation
[OH:1][CH:2]1[CH2:5][CH:4]([C:6]([OH:8])=[O:7])[CH2:3]1.[C:9](Cl)(=[O:11])[CH3:10]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:9]([O:1][CH:2]1[CH2:5][CH:4]([C:6]([OH:8])=[O:7])[CH2:3]1)(=[O:11])[CH3:10]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 3-hydroxycyclobutanecarboxylic acid (100 mg, 0.86 mmol) in DCM (10 mL) was added DMAP (1.0 mg, 0.086 mmol). The solution was cooled to 0° C., followed by the addition of acetyl chloride (0.14 mL, 2.6 mmol). The reaction was heated at 45° C. for 4 hours, then cooled to rt and diluted with DCM (20 mL). The mixture was washed with water (10 mL), followed by washing with brine (10 mL), dried over anhydrous Na2SO4, filtered, and concentrated in vacuo to obtained the crude product which was used in the next step without further purification.
Workup
- temperatureThe reaction was heated at 45° C. for 4 hours
- temperaturecooled to rt
- washThe mixture was washed with water (10 mL)
- washby washing with brine (10 mL)
- dry with materialdried over anhydrous Na2SO4
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-a0a0d8966cd64f768f450299f11628fa
- Source dataset
- uspto-grants-2015_03
- Patent number
- US08975282B2
Reaction notes
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