Benzenemethanethiol, alpha,alpha-diphenyl- → HCID 13456947, compound

HRID 1731687Notes

Reaction equation

HRID 1731687 reaction equation
[C:1]1([C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[SH:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:21]([C:23]1[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=1)#[CH:22].CC(C)([O-])C.[K+]>O1CCCC1>[C:7]([S:8]/[CH:22]=[CH:21]\[C:23]1[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=1)([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)([C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 77281Benzenemethanethiol, alpha,alpha-diphenyl-HCID 1860033-EthynylpyridineHCID 23665647Potassium tert-butoxide

Product 1

HCID 13456947HCID 13456947, compoundYield 60.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of triphenylmethanethiol (1.41 g) and 3-ethynylpyridine (0.5 g) in anhydrous tetrahydrofuran (10 ml) was added potassium t-butoxide (571 mg) at ambient temperature. The mixture was refluxed for 2 hours. After the reaction mixture was cooled to ambient temperature, the reaction mixture was poured into ice-water. The mixture was extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate and concentrated in vacuo to give a crystal. The crystal was washed with ethanol and dried to give 3-[(Z)-2-(tritylthio)vinyl]pyridine (1.11 g).

Workup

  1. temperatureThe mixture was refluxed for 2 hours
  2. extractionThe mixture was extracted with ethyl acetate
  3. washThe extract was washed with a saturated aqueous solution of sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customto give a crystal
  7. washThe crystal was washed with ethanol
  8. customdried

Sources & evidence

ORD record
ord-c073c959413a4a92baab85cad05755e8
Source dataset
uspto-grants-1986_11
Patent number
US04622318

Reaction notes

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