HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Hydrochloric Acid → 4-{3-[(4-acetyl-3-fluorophenyl)thio]phenyl}tetrahydro-2H-pyran-4-carboxamide

HRID 501502
Notes
Print preview

Reaction equation

HRID 501502 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7](F)=[CH:6][C:5]=1[F:11])=[O:3].C([Si](C(C)C)(C(C)C)[S:16][C:17]1[CH:18]=[C:19]([C:23]2([C:29]([NH2:31])=[O:30])[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)[CH:20]=[CH:21][CH:22]=1)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.CC(C)([O-])C.[K+].Cl>C(OCC)(=O)C.C1(C)C=CC=CC=1>[C:2]([C:4]1[CH:9]=[CH:8][C:7]([S:16][C:17]2[CH:18]=[C:19]([C:23]3([C:29]([NH2:31])=[O:30])[CH2:28][CH2:27][O:26][CH2:25][CH2:24]3)[CH:20]=[CH:21][CH:22]=2)=[CH:6][C:5]=1[F:11])(=[O:3])[CH3:1]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 677702,4-DifluoroacetophenoneHCID 2724141Tetrabutylammonium FluorideHCID 23665647Potassium tert-butoxideHCID 566014104-(3-(triisopropylsilylthio)phenyl)tetrahydro-2H-pyran-4-carboxamide

Product 1

HCID 59424843
4-{3-[(4-acetyl-3-fluorophenyl)thio]phenyl}tetrahydro-2H-pyran-4-carboxamide

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

2,4-Difluoroacetophenone (0.40 g, 2.54 mmols), 4-{3-[(triisopropylsilyl)thio]phenyl}-tetra-hydro-2H-pyran-4-carboxamide (1.0 g, 2.54 mmols), tetrabutylammonium fluoride (0.66 g, 2.54 mmols), and potassium tert-butoxide (1.0 M in THF, 2.54 ml, 2.54 mmols) were added to anhydrous toluene (10 ml). The mixture was warmed to 90 degrees Celcius and stirred for 4 hours. After cooling to room temperature, ethyl acetate was added (100 ml) along with 1.0 N HCl (6 ml). The mixture was then stirred for 30 minutes and a beige precipate was collected by suction filtration. The crude product was purified further on silica gel eluting with a 70:30 mixture of methylene chloride and acetone. The appropriate fractions were concentrated to a light brown solid, (0.61 g, 64%).

Workup

  1. temperatureThe mixture was warmed to 90 degrees Celcius
  2. stirringThe mixture was then stirred for 30 minutes
  3. filtrationa beige precipate was collected by suction filtration
  4. customThe crude product was purified further on silica gel eluting with a 70:30 mixture of methylene chloride and acetone
  5. concentrationThe appropriate fractions were concentrated to a light brown solid, (0.61 g, 64%)

Sources & evidence

ORD record
ord-5657c0da012f435683a36db2faaed799
Source dataset
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07772269B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes