Lithium Hydroxide → HCID 58934502, compound

HRID 855161Notes

Reaction equation

HRID 855161 reaction equation
[CH3:1][C:2]1[C:3]([O:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:4][CH:5]=[C:6]2[C:11]=1[O:10][CH:9]([C:12]([F:15])([F:14])[F:13])[C:8]([C:16]([O:18]CC)=[O:17])=[CH:7]2.[Li+].[OH-]>C1COCC1.CCO.O.Cl.CC#N.CN(C=O)C>[CH3:1][C:2]1[C:3]([O:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:4][CH:5]=[C:6]2[C:11]=1[O:10][CH:9]([C:12]([F:15])([F:13])[F:14])[C:8]([C:16]([OH:18])=[O:17])=[CH:7]2

Participants

7

Reactant 2

HCID 3939Lithium HydroxideHCID 69517855HCID 69517855, compound

Product 1

HCID 58934502HCID 58934502, compoundYield 55%

Reagents, catalysts & solvents 4

HCID 313Hydrochloric AcidSolventHCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolventHCID 18504229Ethanol tetrahydrofuran waterSolvent

Conditions

Temperature
60 °C

Procedure

To 0.090 g (0.24 mmol) of ethyl 8-methyl-7-phenoxy-2-(trifluoromethyl)-2H-chromene-3-carboxylate in 5 mL THF:EtOH:H2O (7:2:1) was added 0.015 g (0.36 mmol) of LiOH. The mixture was heated at 60° C. for 2 hours. Removed volatiles in vacuo and diluted with HCl (10%), CH3CN, and DMF and purified by reverse phase chromatography to afford 0.046 g (55%) of a pale yellow solid: 11H NMR (CH3OD/400 MHz) 2.15 (s, 3H), 5.79 (q, 1H, J=7.2 Hz), 6.43 (d, 1H, J=8.4 Hz), 6.94-6.96 (m, 2H), 7.09-7.14 (m, 2H), 7.33-7.37 (m, 2H), 7.74 (s, 1H); MS (ES+) 351.2 (M+H, 100); HRMS (ES−) m/z calcd for (C18H13F3O4) 349.0688, found 349.0681.

Workup

  1. custompurified by reverse phase chromatography

Sources & evidence

ORD record
ord-d2aa963468474cc1a0ff83fa1a795396
Source dataset
uspto-grants-2007_08
Patent number
US07259266B2

Reaction notes

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