Potassium Carbonate → HCID 67472849, compound

HRID 876066Notes

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-6556399c5323460abc739c735364c7b0
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08985753B2

Reaction notes

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