Aluminum(III) Chloride → HCID 53359012, compound

HRID 714497Notes

Reaction equation

C[O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7](=[O:34])[C:8]([C:24]3[CH:33]=[CH:32][C:27]([C:28]([O:30]C)=[O:29])=[CH:26][CH:25]=3)=[C:9]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([C:20]([O:22]C)=[O:21])=[CH:16][CH:15]=3)[S:10]2)=[CH:5][CH:4]=1.[Cl-].[Cl-].[Cl-].[Al+3]>CCOC(C)=O>[C:20]([C:17]1[CH:16]=[CH:15][C:14]([CH2:13][C:9]2[S:10][C:11]3[C:6]([C:7](=[O:34])[C:8]=2[C:24]2[CH:33]=[CH:32][C:27]([C:28]([OH:30])=[O:29])=[CH:26][CH:25]=2)=[CH:5][CH:4]=[C:3]([OH:2])[CH:12]=3)=[CH:19][CH:18]=1)([OH:22])=[O:21]

Participants

Conditions

Temperature: 130 °C

Procedure

Synthesis: Step 1: Synthesis of methyl 4-(7-methoxy-2-(4-(methoxycarbonyl)benzyl)-4-oxo-4H-thiochromen-3-yl)benzoate. Aluminum trichloride (253 mg, 1.9 mmol) was added to Intermediate E (methyl 4-(2-(3-methoxyphenylthio)-2-oxoethyl)benzoate) (500 mg, 1.58 mmol) and the mixture was heated at 130° C. for 1 hour. After cooling to room temperature, the reaction mixture was dissolved in EtOAc (50 ml) and washed with 1 N icy HCl (25 ml×2), water (25 ml) and brine (25 ml), dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by Combi-Flash (40 g silica gel, fluent: PE:EtOAc=10:0 to 1:1 by gradient, 40 ml/min, 30 min, 1.2 L total solvent volume) to afford product as a yellow solid (160 mg, 21%). MS (ESI): m/z 475.1 [M+1]+.

Workup

customSynthesis
temperatureAfter cooling to room temperature
washwashed with 1 N icy HCl (25 ml×2), water (25 ml) and brine (25 ml)
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was purified by Combi-Flash (40 g silica gel, fluent: PE:EtOAc=10:0 to 1:1 by gradient, 40 ml/min, 30 min, 1.2 L total solvent volume)

Sources & evidence

ORD record: ord-6f719ff693574eeca7d3ca4dc7b58eb6
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09187447B2

Reaction notes

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