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Pyridine → 6-Decyl-3-methylthio-2-(trifluoromethanesulfonyloxy)naphthalene

HRID 1476373
Notes
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Reaction equation

HRID 1476373 reaction equation
FC(F)(F)S([O:6][S:7]([C:10]([F:13])([F:12])[F:11])(=[O:9])=[O:8])(=O)=O.ClCCl.[CH2:19]([C:29]1[CH:30]=[C:31]2[C:36](=[CH:37][CH:38]=1)[CH:35]=[C:34](O)[C:33]([S:40][CH3:41])=[CH:32]2)[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28].N1C=CC=CC=1>O.Cl>[CH2:19]([C:29]1[CH:30]=[C:31]2[C:36](=[CH:37][CH:38]=1)[CH:35]=[C:34]([O:6][S:7]([C:10]([F:11])([F:12])[F:13])(=[O:8])=[O:9])[C:33]([S:40][CH3:41])=[CH:32]2)[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 1049PyridineHCID 6344DichloromethaneHCID 67749Trifluoromethanesulfonic anhydrideHCID 867043886-Decyl-3-methylthio-2-hydroxynaphthalene

Product 1

HCID 867043896-Decyl-3-methylthio-2-(trifluoromethanesulfonyloxy)naphthaleneYield 105.7%

Reagents, catalysts & solvents 2

HCID 313
Hydrochloric Acid
Solvent
HCID 962WaterSolvent

Procedure

Trifluoromethanesulfonic anhydride (3 ml, 15 mmol) was added to a dichloromethane (50 ml) solution of the obtained 6-decyl-3-methylthio-2-hydroxynaphthalene (3.63 g, 10 mmol) and pyridine (2.5 ml, 30 mmol) at 0° C. This solution was stirred at room temperature for 25 minutes. Then, the mixture was diluted with water (20 ml), and hydrochloric acid (4 M, 20 ml) was added. The mixture was extracted with dichloromethane (30 ml×3). The organic phases obtained by repeating the extraction three times were collected, washed with saturated saline water (30 ml×3), dried with MgSO4, and condensed to obtain 6-decyl-3-methylthio-2-(trifluoromethanesulfonyloxy)naphthalene (compound (4)-81) (4.89 g, 99%).

Workup

  1. additionwas added
  2. extractionThe mixture was extracted with dichloromethane (30 ml×3)
  3. customThe organic phases obtained
  4. extractionthe extraction three times
  5. customwere collected
  6. washwashed with saturated saline water (30 ml×3)
  7. dry with materialdried with MgSO4, and condensed

Sources & evidence

ORD record
ord-ed4e1ddcc0824711a242da0d5b994ca5
Source dataset
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09018630B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes