Carbon Dioxide → HCID 178448133, compound

HRID 484319

Reaction equation

HRID 484319 reaction equation
[F:1][C:2]1[C:10]([F:11])=[C:9]([O:12][CH2:13][CH3:14])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].F[C:16]1[C:21](F)=[CH:20][CH:19]=[CH:18][C:17]=1O.S(O[CH2:31][CH3:32])(OCC)(=O)=O.[C:33](=O)([O-])[O-].[K+].[K+].FC1C(F)=CC=CC=1OCC.C([Li])CCC.CN(C)CCN(C)C.C(=O)=O.C([C@H]1CC[C@H](O)CC1)CC.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C=O.O1CCCC1.CN(C)C1C=CN=CC=1.ClCCl>[F:1][C:2]1[C:10]([F:11])=[C:9]([O:12][CH2:13][CH3:14])[CH:8]=[CH:7][C:3]=1[C:4]([O:6][C@H:20]1[CH2:21][CH2:16][C@H:17]([CH2:33][CH2:31][CH3:32])[CH2:18][CH2:19]1)=[O:5]

Participants

13

Reactant 8

HCID 280Carbon DioxideHCID 10868DicyclohexylcarbodiimideHCID 808792,3-DifluorophenolHCID 27694004-Ethoxy-2,3-difluorobenzoic acidHCID 27829281-Ethoxy-2,3-DifluorobenzeneHCID 86747043Diethyl sulfate potassium carbonateHCID 178448131HCID 178448131, compoundHCID 178483778HCID 178483778, compound

Product 1

HCID 178448133HCID 178448133, compound

Reagents, catalysts & solvents 4

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

0.1 mol of 2,3-difluoro-4-ethoxybenzoic acid (preparable from 2,3-difluorophenol by alkylation using diethyl sulfate/potassium carbonate in dimethylformamide, metallation of the 2,3-difluorophenetole in the 4-position using butyllithium/tetramethylethylenediamine in tetrahydrofuran (THF) at -70° to -80° and reaction with solid carbon dioxide), 0.01 mol of 4-dimethylaminopyridine and 0.1 mol of trans-4-propylcyclohexanol are initially introduced in 150 ml of dichloromethane, a solution of 0.1 mol of dicyclohexylcarbodiimide in 30 ml of dichloromethane is added dropwise at 10° with stirring, and the mixture is subsequently stirred at room temperature for 15 hours. The mixture is filtered through silica gel with suction, the solvent is evaporated, and trans-4-propylcyclohexyl 2,3-difluoro-4-ethoxybenzoate is obtained as a residue and is purified by crystallization. Mp. 93°, cp. (48°).

Workup

  1. customat -70° to -80°
  2. stirringthe mixture is subsequently stirred at room temperature for 15 hours
  3. filtrationThe mixture is filtered through silica gel with suction
  4. customthe solvent is evaporated

Sources & evidence

ORD record
ord-c0a7ba1d70d94fcfa35835ddd9b19302
Source dataset
uspto-grants-1993_07
Patent number
US05230827

Linked notes

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