Diethyl Ether → HCID 178447918, compound

HRID 1265958

Reaction equation

HRID 1265958 reaction equation
[F:1][C:2]1[C:7]([F:8])=[C:6]([C@H:9]2[CH2:14][CH2:13][C@H:12]([CH2:15][CH2:16][CH3:17])[CH2:11][CH2:10]2)[CH:5]=[CH:4][C:3]=1[OH:18].C(OCC)C.[F:24][C:25]1[C:33]([F:34])=[C:32]([O:35][CH2:36][CH3:37])[CH:31]=[CH:30][C:26]=1[C:27](O)=[O:28]>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH2:36]([O:35][C:32]1[CH:31]=[CH:30][C:26]([C:27]([O:18][C:3]2[CH:4]=[CH:5][C:6]([C@H:9]3[CH2:10][CH2:11][C@H:12]([CH2:15][CH2:16][CH3:17])[CH2:13][CH2:14]3)=[C:7]([F:8])[C:2]=2[F:1])=[O:28])=[C:25]([F:24])[C:33]=1[F:34])[CH3:37]

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 27694004-Ethoxy-2,3-difluorobenzoic acidHCID 178447914HCID 178447914, compound

Product 1

HCID 178447918HCID 178447918, compoundYield 99.7%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

In a 500 mL three-neck flask, 3.20 g of 2,3-difluoro-4-ethoxybenzoic acid (a) and 3.84 g of 2,3-difluoro-4-(trans-4-propylcyclohexyl)phenol (1) were dissolved in 230 mL of methylene chloride. 0.70 g of 4-dimethylaminopyridine was added thereto and stirred at room temperature for 1 hour. A solution in which 3.54 g of N,N-dicyclohexylcarbodiimide was dissolved in 90 mL of methylene chloride was added thereto and stirred overnight. Diethyl ether was added and urea precipitated was filtered off. Saturated aqueous solution of sodium chloride was added and stirred for 1 hour. After organic layer was separated, the organic layer was washed with 3N hydrochloric acid and saturated aqueous solution of sodium bicarbonate, and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to give 6.60 g of 2,3-difluoro-4-(trans-4-propylcyclohexyl)phenyl 4-ethoxy-2,3-difluorobenzoate (m).

Workup

  1. additionwas added
  2. stirringstirred overnight
  3. customurea precipitated
  4. filtrationwas filtered off
  5. additionSaturated aqueous solution of sodium chloride was added
  6. stirringstirred for 1 hour
  7. customAfter organic layer was separated
  8. washthe organic layer was washed with 3N hydrochloric acid and saturated aqueous solution of sodium bicarbonate
  9. dry with materialdried over anhydrous sodium sulfate
  10. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-dba73a9fc9bd4f41a61c5117f7d4f0b0
Source dataset
uspto-grants-2003_04
Patent number
US06548126B1

Linked notes

Loading…