Potassium Carbonate → HCID 67472849, compound

HRID 409529Notes

Reaction equation

[OH:1][CH:2]([CH2:21][OH:22])[CH2:3][O:4][C:5]1[C:18]2[S:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10](=[O:19])[C:9]=2[C:8]([F:20])=[CH:7][CH:6]=1.Cl[CH2:24][CH2:25][C:26](Cl)=[O:27].C(=O)([O-])[O-].[K+].[K+].[C:35]([C:39]1C=C(C)C=C(C(C)(C)C)[C:40]=1[OH:50])(C)(C)C>ClCCl.C(#N)C>[C:26]([O:1][CH:2]([CH2:3][O:4][C:5]1[C:18]2[S:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10](=[O:19])[C:9]=2[C:8]([F:20])=[CH:7][CH:6]=1)[CH2:21][O:22][C:40](=[O:50])[CH:39]=[CH2:35])(=[O:27])[CH:25]=[CH2:24]

Participants

Conditions

Temperature: 81 °C

Procedure

4-(2,3-dihydroxy-propoxy)-1-fluoro-thioxanthen-9-one (2.9 g, 9 mmol), 3-chloropropionyl chloride (9.5 g, 75 mmol), potassium carbonate (10.4 g, 75 mmol) and 2,6-di-tert-butyl-4-methylphenol (0.1 g, 0.00045 mol) were added to acetonitrile (35 mL). The reaction mixture was heated at 81° C. and stirred for 6 hours. After cooling down to room temperature, dichloromethane (200 mL) was added and the reaction mixture was extracted with distilled water (200 mL). The organic layer was separated, dried over MgSO4 and evaporated under reduced pressure. The product was purified on a Prochrom LC 80 Column using dichloromethane/ethyl acetate (98/2) as eluent and Kromasil Si60A 10 μm as packing material, to yield 1.2 g of acrylic acid 2-acryloyloxy-3-(1-fluoro-9-oxo-9H-thioxanthen-4-yloxy)-propyl ester.

Workup

temperatureAfter cooling down to room temperature
extractionthe reaction mixture was extracted with distilled water (200 mL)
customThe organic layer was separated
dry with materialdried over MgSO4
customevaporated under reduced pressure
customThe product was purified on a Prochrom LC 80 Column

Sources & evidence

ORD record: ord-33f7df40c4fd4c7d859d579105defe1a
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08759412B2

Reaction notes

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