1-(4-Hydroxynaphthalen-1-yl)thiolan-1-ium chloride → HCID 86662326, compound

HRID 2405631Notes

Reaction equation

HRID 2405631 reaction equation
[F:1][C:2]([F:25])([S:21]([O-:24])(=[O:23])=[O:22])[CH:3]([O:8][C:9]([C:11]12[CH2:20][CH:15]3[CH2:16][CH:17]([CH2:19][CH:13]([CH2:14]3)[CH2:12]1)[CH2:18]2)=[O:10])[C:4]([F:7])([F:6])[F:5].[Na+].[Cl-].[OH:28][C:29]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[C:32]([S+:39]2[CH2:43][CH2:42][CH2:41][CH2:40]2)=[CH:31][CH:30]=1>>[C:11]12([C:9]([O:8][CH:3]([C:4]([F:7])([F:5])[F:6])[C:2]([F:1])([F:25])[S:21]([O-:24])(=[O:22])=[O:23])=[O:10])[CH2:12][CH:13]3[CH2:19][CH:17]([CH2:16][CH:15]([CH2:14]3)[CH2:20]1)[CH2:18]2.[OH:28][C:29]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[C:32]([S+:39]2[CH2:40][CH2:41][CH2:42][CH2:43]2)=[CH:31][CH:30]=1

Participants

3

Reactant 2

HCID 714422161-(4-Hydroxynaphthalen-1-yl)thiolan-1-ium chlorideHCID 86662327Sodium 1,1,3,3,3-pentafluoro-2-(adamantane-1-carbonyloxy)propanesulfonate

Product 1

HCID 86662326HCID 86662326, compoundYield 43%

Procedure

An aqueous solution of sodium 1,1,3,3,3-pentafluoro-2-(adamantane-1-carbonyloxy)propanesulfonate (corresponding to 0.021 mol) synthesized according to the formulation described in JP-A 2007-145797 was mixed with the aqueous solution of 4-hydroxynaphthyl-1-tetrahydrothiophenium chloride (corresponding to 0.023 mol) synthesized in Reference Synthesis Example 1. The mixture was extracted with 100 g of dichloromethane and 50 g of methyl isobutyl ketone. The organic layer was washed with water, and the solvent was distilled off in vacuum. The residue was poured into isopropyl ether for crystallization, filtered and dried, obtaining the target compound. White crystal, 6.2 g, yield 43%.

Workup

  1. customsynthesized in Reference Synthesis Example 1
  2. extractionThe mixture was extracted with 100 g of dichloromethane and 50 g of methyl isobutyl ketone
  3. washThe organic layer was washed with water
  4. distillationthe solvent was distilled off in vacuum
  5. additionThe residue was poured into isopropyl ether for crystallization
  6. filtrationfiltered
  7. customdried
  8. customobtaining the target compound

Sources & evidence

ORD record
ord-f3337d57a91143e79c79a75604258d92
Source dataset
uspto-grants-2014_08
Patent number
US08808964B2

Reaction notes

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