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((2R)-8-(2-chlorophenyl)-7-fluoro-2H-chromen-2-yl)methyl 4-methylbenzenesulfonate → ((2R)-8-(2-chlorophenyl)-7-fluorochroman-2-yl)methyl 4-methylbenzenesulfonate

HRID 902367
Notes
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Reaction equation

HRID 902367 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:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[Cl:30])[C:17]([F:23])=[CH:18][CH:19]=3)[O:14]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1>C(O)C.C(OCC)(=O)C.[Pt](=O)=O>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([O:11][CH2:12][C@H:13]2[CH2:22][CH2:21][C:20]3[C:15](=[C:16]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[Cl:30])[C:17]([F:23])=[CH:18][CH:19]=3)[O:14]2)(=[O:10])=[O:9])=[CH:6][CH:7]=1
ParticipantsProcedureSources & evidenceReaction notes

Participants

5

Reactant 1

HCID 86609141((2R)-8-(2-chlorophenyl)-7-fluoro-2H-chromen-2-yl)methyl 4-methylbenzenesulfonate

Product 1

HCID 86609143((2R)-8-(2-chlorophenyl)-7-fluorochroman-2-yl)methyl 4-methylbenzenesulfonateYield 100%

Reagents, catalysts & solvents 3

HCID 345198Adams' catalystCatalystHCID 702EthanolSolventHCID 8857
Ethyl Acetate
Solvent

Procedure

Treatment of ((2R)-8-(2-chlorophenyl)-7-fluoro-2H-chromen-2-yl)methyl 4-methylbenzenesulfonate (0.7 g, 1.57 mmol) in ethanol (40 mL) and ethyl acetate (10 mL) with platinum (IV) oxide (84% Pt, 0.21 g) according to the procedure described for Example 69, Step 8 provided 0.7 g (100%) of ((2R)-8-(2-chlorophenyl)-7-fluorochroman-2-yl)methyl 4-methylbenzenesulfonate as a pale yellow oil.

Sources & evidence

ORD record
ord-3b0bf13ab8a84da097af4bb4362cf8f8
Source dataset
uspto-grants-2008_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07365095B2

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes