Sodium Hydroxide → HCID 21097637, compound

HRID 1351059Notes

Reaction equation

HRID 1351059 reaction equation
[F:1][C:2]([F:8])([F:7])[S:3]([O-:6])(=[O:5])=[O:4].F[C:10]1[CH:15]=[CH:14][C:13]([S+:16]([C:23]2[CH:28]=[CH:27]C=[CH:25][CH:24]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:12][CH:11]=1.[OH-].[Na+].[CH3:31][C:32]1([CH3:44])[CH2:37][O:36][C:35]2([CH2:42][CH2:41][CH2:40][CH2:39][CH:38]2S)[O:34][CH2:33]1>ClCCl>[F:1][C:2]([F:8])([F:7])[S:3]([O-:6])(=[O:5])=[O:4].[CH3:31][C:32]1([CH3:44])[CH2:37][O:36][C:35]2([CH2:42][CH2:41][CH2:40][CH2:39][CH:38]2[S:3]([C:2]2[CH:27]=[CH:28][C:23]([S+:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:13]3[CH:12]=[CH:11][CH:10]=[CH:15][CH:14]=3)=[CH:24][CH:25]=2)(=[O:6])=[O:4])[O:34][CH2:33]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 16213837(4-Fluorophenyl)(diphenyl)sulfanium trifluoromethanesulfonateHCID 21097623HCID 21097623, compound

Product 1

HCID 21097637HCID 21097637, compoundYield 125.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

26.7 g of 4-fluorophenyl diphenylsulfonium trifluoromethanesulfonate was dissolved in 200 g of dichloromethane in a reaction flask, in which the atmosphere was replaced with nitrogen. 200 g of 10 wt % sodium hydroxide aqueous solution and 14.6 g of 3,3-dimethyl-1,5-dioxaspiro[5.5]undecane-7-thiol were added. The mixture was stirred at 30 minutes for room temperature and transferred to a separatory funnel, shaken, and allowed to stand still. The water layer was removed. After the addition of 300 ml of distilled water, the mixture was further shaken and allowed to stand still. The water layer was removed. The resulting dichloromethane solution was dried with anhydrous magnesium sulfate and filtered. After evaporating dichloromethane from the dried solution, the residual liquid was dried under reduced pressure to obtain 25.6 g of [4-(3,3-dimethyl-1,5-dioxaspiro[5.5]undecan-7-ylsulfonyl)phenyl]diphenylsulfonium trifluoromethanesulfonate.

Workup

  1. customtransferred to a separatory funnel
  2. stirringshaken
  3. customThe water layer was removed
  4. additionAfter the addition of 300 ml of distilled water
  5. stirringthe mixture was further shaken
  6. customThe water layer was removed
  7. dry with materialThe resulting dichloromethane solution was dried with anhydrous magnesium sulfate
  8. filtrationfiltered
  9. customAfter evaporating dichloromethane from the dried solution
  10. customthe residual liquid was dried under reduced pressure

Sources & evidence

ORD record
ord-80163d4c70b249a0aa9b581605d17da5
Source dataset
uspto-grants-2007_05
Patent number
US07217492B2

Reaction notes

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