Ammonium Chloride → HCID 67438855, compound

HRID 1890264Notes

Reaction equation

HRID 1890264 reaction equation
C([Li])CCC.[CH2:6]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:7][C:8]#[CH:9].[F:18][C:19]1[CH:27]=[CH:26][C:22]([C:23](Cl)=[O:24])=[CH:21][CH:20]=1.[Cl-].[NH4+]>C1COCC1>[CH2:11]([O:10][CH2:6][CH2:7][C:8]#[C:9][C:23]([C:22]1[CH:26]=[CH:27][C:19]([F:18])=[CH:20][CH:21]=1)=[O:24])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 678794-Fluorobenzoyl chlorideHCID 11008213Benzene, [(3-butynyloxy)methyl]-HCID 178418339Butyllithium

Product 1

HCID 67438855HCID 67438855, compoundYield 48.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

At −70° C., 2.56 ml of a 1.6 M butyllithium solution are added dropwise to a solution of 505 mg (3.15 mmol) of benzyl but-3-yn-1-yl ether in 10 ml of THF, and the mixture is stirred for 30 min. 500 mg (5.15 mmol) of 4-fluorobenzoyl chloride are added dropwise to this solution, and the temperature is allowed to rise to 0° C. After 1 h, 10 ml of a saturated ammonium chloride solution are added, and the reaction mixture is extracted with 3×50 ml of ethyl acetate. The combined organic phases are washed with water, dried over MgSO4 and freed from the solvent under reduced pressure. Purification by column chromatography on silica gel (cyclohexane/ethyl acetate) gives 430 mg (45%) of the desired product; log P(HCOOH): 3.89; 1H-NMR (DMSO-d6): 8.15 (dd, 2H), 7.34 (m, 7H), 4.57 (s, 2H), 3.70 (t, 2H), 2.90 (t, 2H).

Workup

  1. customto rise to 0° C
  2. waitAfter 1 h
  3. extractionthe reaction mixture is extracted with 3×50 ml of ethyl acetate
  4. washThe combined organic phases are washed with water
  5. dry with materialdried over MgSO4
  6. customPurification by column chromatography on silica gel (cyclohexane/ethyl acetate)

Sources & evidence

ORD record
ord-3014cfd2d721473b925383053420ad3a
Source dataset
uspto-grants-2013_08
Patent number
US08507472B2

Reaction notes

Loading…