Benzyl mercaptan → HCID 86680450, compound

HRID 240439Notes

Reaction equation

HRID 240439 reaction equation
[CH2:1]([SH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C)([O-])C.[K+].O1CCCC1.Br[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([CH3:30])([CH3:29])[CH3:28])[N:22]=1>CN(C)C=O.O>[CH2:1]([S:8][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([CH3:30])([CH3:29])[CH3:28])[N:22]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 7509Benzyl mercaptanHCID 8028TetrahydrofuranHCID 221134152-Bromo-6-tert-butylpyridineHCID 23665647Potassium tert-butoxide

Product 1

HCID 86680450HCID 86680450, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of benzyl mercaptan (0.22 mL, 1.87 mmol) in anhydrous N,N-dimethylformamide (10 mL) was added a 1.0 M solution of potassium tert-butoxide in tetrahydrofuran (1.87 mL, 1.87 mmol) dropwise over 2 minutes. To the resulting suspension was added 2-bromo-6-tert-butylpyridine (0.20 g, 0.93 mmol), and the resulting mixture was stirred at 50° C. for 16 hours. The cooled mixture was poured into water (50 mL) and extracted with ethyl acetate (50 mL), and the ethyl acetate layer was dried over Na2SO4, filtered and concentrated in vacuo to give a crude product. Purification by column chromatography on silica gel using hexanes gave the titled compound. 1H NMR (300 MHz, CDCl3) δ ppm 1.35 (s, 9H), 4.50 (s, 2H), 6.93-7.03 (m, 2H), 7.17-7.45 (m, 6H); MS (APCI) m/z 258.3 (M+H)+.

Workup

  1. extractionextracted with ethyl acetate (50 mL)
  2. dry with materialthe ethyl acetate layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto give a crude product
  6. customPurification by column chromatography on silica gel

Sources & evidence

ORD record
ord-af3ead02ed3f41df86fc8958445547bc
Source dataset
uspto-grants-2014_02
Patent number
US08648074B2

Reaction notes

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