HCID 86609102, compound → HCID 86609104, compound

HRID 902304Notes

Reaction equation

HRID 902304 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([O:11][CH2:12][C@H:13]2[CH:22]=[CH:21][C:20]3[C:15](=[C:16]([C:23]4[C:28]([Cl:29])=[CH:27][CH:26]=[CH:25][C:24]=4[Cl:30])[CH:17]=[CH:18][CH:19]=3)[O:14]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[H][H]>C(OCC)(=O)C.C(O)C.[Pt](=O)=O>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([O:11][CH2:12][C@H:13]2[CH2:22][CH2:21][C:20]3[C:15](=[C:16]([C:23]4[C:24]([Cl:30])=[CH:25][CH:26]=[CH:27][C:28]=4[Cl:29])[CH:17]=[CH:18][CH:19]=3)[O:14]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 86609102HCID 86609102, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86609104HCID 86609104, compoundYield 64.6%

Reagents, catalysts & solvents 3

HCID 345198Adams' catalystCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of [(2R)-8-(2,6-dichlorophenyl)-2H-chromen-2-yl]methyl 4-methylbenzenesulfonate (0.846 g, 1.83 mmol) in ethyl acetate (10 mL) was added to a suspension of platinum (IV) oxide (45 mg, 0.198 mmol) in absolute ethanol (30 mL) and the mixture hydrogenated at 10 psi of hydrogen for 100 minutes. The reaction mixture was then filtered through celite and the filtrate concentrated under reduced pressure to afford a brown syrup. Purification by flash chromatography using a solvent gradient of 5 to 20% ethyl acetate in hexane afforded 0.548 g (64%) of [(2R)-8-(2.6-dichlorophenyl)-3,4-dihydro-2H-chromen-2-yl]methyl 4-methylbenzenesulfonate as a yellow solid. HRMS: calcd for C23H20Cl2O4S+H+, 463.0532 1. found (ESI, [M+H]+), 463.0555.

Workup

  1. filtrationThe reaction mixture was then filtered through celite
  2. concentrationthe filtrate concentrated under reduced pressure
  3. customto afford a brown syrup
  4. customPurification by flash chromatography

Sources & evidence

ORD record
ord-7d32693ed5cb4287a60a9ef579297239
Source dataset
uspto-grants-2008_04
Patent number
US07365095B2

Reaction notes

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