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Ethanethiol → HCID 10298833, compound

HRID 2213168
Notes
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Reaction equation

HRID 2213168 reaction equation
C(S)C.[Li]CCCC.Cl.[N:10]1([CH2:16][CH2:17][O:18][C:19]2[CH:45]=[CH:44][C:22]([O:23][C:24]3[C:33]4[C:28](=[CH:29][C:30]([O:34]C)=[CH:31][CH:32]=4)[CH:27]=[CH:26][C:25]=3[C:36]3[CH:41]=[CH:40][CH:39]=[C:38]([O:42][CH3:43])[CH:37]=3)=[CH:21][CH:20]=2)[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1.[Li]SCC>CN(C=O)C.CCCCCC.[Li]>[N:10]1([CH2:16][CH2:17][O:18][C:19]2[CH:20]=[CH:21][C:22]([O:23][C:24]3[C:33]4[C:28](=[CH:29][C:30]([OH:34])=[CH:31][CH:32]=4)[CH:27]=[CH:26][C:25]=3[C:36]3[CH:41]=[CH:40][CH:39]=[C:38]([O:42][CH3:43])[CH:37]=3)=[CH:44][CH:45]=2)[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 6343EthanethiolHCID 98713381-[4-[2-(1-Piperidinyl)-ethoxy]phenoxy]-2-(3-methoxyphenyl)-6-methoxynaphthalene hydrochlorideHCID 178418339ButyllithiumHCID 178506962HCID 178506962, compound

Product 1

HCID 10298833HCID 10298833, compoundYield 53.7%

Reagents, catalysts & solvents 3

HCID 6228
Dimethylformamide
Solvent
HCID 8058HexaneSolvent
HCID 3028194LithiumSolvent

Procedure

A solution of ethanethiol (2.85 ml) in anhydrous DMF (125 mL) under N2 atmosphere was cooled in an ice bath and treated dropwise with 20.1 mL of 1.6 M n-BuLi in hexane. The resulting solution, which was approximately 0.22 M in lithium thioethylate (LiSEt) was allowed to warm to ambient temperature prior to its use. To 1-[4-[2-(1-piperidinyl)-ethoxy]phenoxy]-2-(−3-methoxyphenyl)-6-methoxynaphthalene hydrochloride (0.550 g, 1.05 mmol) under nitrogen atmosphere was added 70 mL (15.4 mmol) of the LiSEt solution and the resulting reaction mixture was heated in a 107° C. oil bath for 5 hr. The resulting yellow solution was concentrated under reduced pressure to remove most of the solvent and the yellow oil concentrate was distributed between 300 mL of ethyl acetate and 1N HCl (100 mL) to which 50 g of ice had been added. The ethyl acetate layer extract was washed with 4×25 mL portions of brine, dried over magnesium sulfate, filtered, and concentrated to a foul-smelling yellow oil. The crude material was purified in portions by radial chromatography that employed 5% methanol in chloroform as the elution solvent. The appropriate fractions were combined, concentrated, and dried in vacuo to provide 265 mg (53%) of 1-[4-[2-(1-piperidinyl)ethoxy]-phenoxy]-2-(3-methoxyphenyl)-6-hydroxynapht-halene, as a grey foam.

Workup

  1. customthe resulting reaction mixture
  2. temperaturewas heated in a 107° C. oil bath for 5 hr
  3. concentrationThe resulting yellow solution was concentrated under reduced pressure
  4. customto remove most of the solvent
  5. concentrationthe yellow oil concentrate
  6. additionhad been added
  7. extractionThe ethyl acetate layer extract
  8. washwas washed with 4×25 mL portions of brine
  9. dry with materialdried over magnesium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated to a foul-smelling yellow oil
  12. customThe crude material was purified in portions by radial chromatography
  13. concentrationconcentrated
  14. customdried in vacuo

Sources & evidence

ORD record
ord-52cfefc7be684749abbe870e738d63d9
Source dataset
uspto-grants-2006_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07105541B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes