Hydrochloric Acid → HCID 57871420, compound

HRID 550215Notes

Reaction equation

HRID 550215 reaction equation
N1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:7][C:8]([F:21])([F:20])[S:9]([O:12]S(C(F)(F)F)(=O)=O)(=[O:11])=[O:10].Cl.[OH2:23]>CCOC(C)=O>[CH2:3]([C:4]([C:4]1[CH:3]=[C:2]2[C:2]([CH:3]=[CH:4][C:5]([O:12][S:9]([C:8]([F:21])([F:20])[F:7])(=[O:11])=[O:10])=[CH:6]2)=[CH:6][CH:5]=1)([OH:23])[CH2:5][CH3:6])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 1049PyridineHCID 67749Trifluoromethanesulfonic anhydride

Product 1

HCID 57871420HCID 57871420, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Cool a CH2CL2 (30 mL) solution of 7-(1-ethyl-11-hydroxypropyl)naphthalen-2-ol (0.97 g, 4.2 mmol) and pyridine (1.3 mL, 16.3 mmol) with an ice bath. Treat the cooled solution dropwise with trifluoromethanesulfonic anhydride (1.0 mL, 6.1 mmol). Remove the cooling bath and stir the mixture for 1.5 h at RT. Quench the reaction with ice water. Dilute the reaction mixture with EtOAc and water (100 mL each) and acidify to pH 1 using 0.1N HCl. Dry the organic layer over Na2SO4, filter and concentrate the filtrate. Purify by radial silica gel (2:98 to 10:90 EtOAc:hex) to give the title compound as a colorless oil (1.46 g, 66%). MS (ES) m/e 377 (M-NH4).

Workup

  1. customRemove the cooling bath
  2. customQuench
  3. customthe reaction with ice water
  4. dry with materialDry the organic layer over Na2SO4
  5. filtrationfilter
  6. concentrationconcentrate the filtrate
  7. customPurify by radial silica gel (2:98 to 10:90 EtOAc:hex)

Sources & evidence

ORD record
ord-ab3ea6af77d14e91ac0240f8e7909abf
Source dataset
uspto-grants-2011_05
Patent number
US07943795B2

Reaction notes

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