Hydrochloric Acid → HCID 86761766, compound

HRID 386322Notes

Reaction equation

HRID 386322 reaction equation
CO.[CH2:3]([O:5][C:6]1[CH:11]=[CH:10][C:9]([CH:12]2[CH2:17][CH2:16][CH:15]([CH:18]3[CH2:23][O:22][CH:21]([C:24]#[C:25][Si](C)(C)C)[CH2:20][CH2:19]3)[CH2:14][CH2:13]2)=[C:8]([F:30])[C:7]=1[F:31])[CH3:4].[OH-].[Na+].Cl>ClCCl>[CH2:3]([O:5][C:6]1[CH:11]=[CH:10][C:9]([CH:12]2[CH2:17][CH2:16][CH:15]([CH:18]3[CH2:23][O:22][CH:21]([C:24]#[CH:25])[CH2:20][CH2:19]3)[CH2:14][CH2:13]2)=[C:8]([F:30])[C:7]=1[F:31])[CH3:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 69004259HCID 69004259, compound

Product 1

HCID 86761766HCID 86761766, compoundYield 84.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

40 mL of methanol and 30 mL of dichloromethane were added to 3.7 g of (5-[4-(4-ethoxy-2,3-difluorophenyl)cyclohexyl]-tetrahydropyran-2-ylethynyl) trimethylsilane obtained in the seventh step, and the mixture was cooled to 0° C., to which 5 mL of a sodium hydroxide aqueous solution (1M) was added. The temperature of the reaction solution was increased to room temperature, and the reaction solution was stirred for 2 hours, neutralized with hydrochloric acid, and the solvent was concentrated to about 30 mL under reduced pressure. The residue was extracted three times with 20 mL of diethyl ether, and the mixture including the organic layer was washed with water and dried over anhydrous magnesium sulfate, followed by distilling off the solvent. The residue was purified by silica gel column chromatography to provide 2.6 g of 5-[4-(4-ethoxy-2,3-difluorophenyl)cyclohexyl]-2-ethynyltetrahydropyran.

Workup

  1. customobtained in the seventh step
  2. additionwas added
  3. concentrationthe solvent was concentrated to about 30 mL under reduced pressure
  4. extractionThe residue was extracted three times with 20 mL of diethyl ether
  5. washwas washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationby distilling off the solvent
  8. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-12308e7f39c743199bd4f6f1405cc553
Source dataset
uspto-grants-2013_02
Patent number
US08372306B2

Reaction notes

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