Potassium Carbonate → 2-[4-(3-Chloro-propoxy)-benzoyl]-cyclobutanecarboxylic acid ethyl ester

HRID 2042595Notes

Reaction equation

[CH2:1]([O:3][C:4]([CH:6]1[CH2:9][CH2:8][CH:7]1[C:10](=[O:18])[C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1)=[O:5])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Br[CH:26]([Cl:29])[CH2:27][CH3:28]>CC(C)=O>[CH2:1]([O:3][C:4]([CH:6]1[CH2:9][CH2:8][CH:7]1[C:10](=[O:18])[C:11]1[CH:12]=[CH:13][C:14]([O:17][CH2:28][CH2:27][CH2:26][Cl:29])=[CH:15][CH:16]=1)=[O:5])[CH3:2]

Participants

Conditions

Temperature: 70 °C

Procedure

To 2-(4-hydroxy-benzoyl)-cyclobutanecarboxylic acid ethyl ester (0.55 g, 2.20 mmol) in acetone (10 mL) was added potassium carbonate (0.91 g, 6.58 mmol) and 1-bromo-chloropropane (0.26 mL, 2.63 mmol). After overnight stirring at 70° C., the reaction was filtered, partitioned between dichloromethane/water, washed with brine, dried over sodium sulfate, and concentrated. The product was purified using a Single Step column (9:1 hexanes:ethyl acetate) to obtain 0.30 g (42%); MS m/z 325 (M+H).

Workup

filtrationthe reaction was filtered
custompartitioned between dichloromethane/water
washwashed with brine
dry with materialdried over sodium sulfate
concentrationconcentrated
customThe product was purified
customto obtain 0.30 g (42%)

Sources & evidence

ORD record: ord-a38ba8b406124a9e85c4b00f5a812a75
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08586588B2

Reaction notes

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