Phenol → HCID 69517855, compound

HRID 855160Notes

Reaction equation

HRID 855160 reaction equation
F[C:2]1[C:11]([CH3:12])=[C:10]2[C:5]([CH:6]=[C:7]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:8]([C:13]([F:16])([F:15])[F:14])[O:9]2)=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[C:28]1([OH:34])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>CN(C=O)C>[CH3:12][C:11]1[C:2]([O:34][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[CH:3][CH:4]=[C:5]2[C:10]=1[O:9][CH:8]([C:13]([F:16])([F:15])[F:14])[C:7]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:6]2

Participants

5

Reactant 3

HCID 996Phenol2×HCID 11430Potassium Carbonate2×HCID 58935017HCID 58935017, compound

Product 1

HCID 69517855HCID 69517855, compoundYield 28.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To 0.304 g (1.00 mmol) of ethyl 7-fluoro-8-methyl-2-(trifluoromethyl)-2H-chromene-3-carboxylate in 5.0 mL of DMF was added 0.194 g of K2CO3 (1.40 mmol) and 0.105 mL (1.20 mmol) of phenol. The mixture was heated to 90° C. and LC/MS indicated remaining starting material. The mixture was then heated to 110° C. overnight and LC/MS still indicated starting material remaining. Added an additional 0.194 g of K2CO3 (1.40 mmol) and 0.105 mL (1.20 mmol) of phenol. Heated overnight and purified by Gilson reverse phase chromatography to afford 0.107 g (28%) of a pale yellow solid: 1H NMR (CH30D/400 MHz) 1.32 (t, 3H, J=7.2 Hz), 2.15 (s, 3H), 4.24-4.33 (m, 2H), 5.82 (q, 1H, J=7.2 Hz), 6.42 (d, 1H, J=8.4 Hz), 6.94-6.97 (m, 2H), 7.09-7.15 (m, 2H), 7.33-7.37 (m, 2H), 7.75 (s, 1H); MS (ES+) 379.3 (M+H, 100); HRMS (EI+) m/z calcd for (C20H17F3O4) 378.1079, found 378.1062.

Workup

  1. temperatureThe mixture was then heated to 110° C. overnight
  2. temperatureHeated overnight
  3. custompurified by Gilson reverse phase chromatography

Sources & evidence

ORD record
ord-15bb83c31c0a4ecb86b1c657046646cc
Source dataset
uspto-grants-2007_08
Patent number
US07259266B2

Reaction notes

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