Thiazole → HCID 67003630, compound

HRID 2362624Notes

Reaction equation

HRID 2362624 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.C([Li])CCC.[C:11]1(=[O:15])[CH2:14][CH2:13][CH2:12]1.[CH2:16]([Sn:20](Cl)([CH2:25][CH2:26][CH2:27][CH3:28])[CH2:21][CH2:22][CH2:23][CH3:24])[CH2:17][CH2:18][CH3:19]>O1CCCC1>[CH2:25]([Sn:20]([CH2:16][CH2:17][CH2:18][CH3:19])([CH2:21][CH2:22][CH2:23][CH3:24])[C:5]1[S:1][C:2]([C:11]2([OH:15])[CH2:14][CH2:13][CH2:12]2)=[N:3][CH:4]=1)[CH2:26][CH2:27][CH3:28]

Participants

6

Reactant 4

HCID 9256ThiazoleHCID 14496CyclobutanoneHCID 15096Tributyltin ChlorideHCID 178418339Butyllithium2×

Product 1

HCID 67003630HCID 67003630, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a cold (−78° C.) solution of thiazole (1.0 mL, 14.1 mmol) in tetrahydrofuran (70 mL) was added n-butyllithium (11.83 mL, 14.1 mmol, 2.38 M in hexane) dropwise. After 15 minutes, cyclobutanone (1.06 mL, 14.1 mmol) was added in a single portion. The reaction was stirred at −78° C. for 30 minutes, and n-butyllithium (11.83 mL, 14.1 mmol, 2.38 M in hexane) was added dropwise. The reaction was stirred for an additional 20 minutes, after which tributyltin chloride (3.82 mL, 14.1 mmol) was added dropwise. After 10 minutes, the cold reaction was quenched by the addition of saturated aqueous ammonium chloride solution (100 mL) and ethyl acetate (100 mL). The reaction was warmed to ambient temperature. The layers were separated, and the aqueous layer was extracted with additional ethyl acetate (2×100 mL). The combined organics were dried with anhydrous Na2SO4, filtered, and concentrated. Trituration of the residue with hexane gave the title compound, which was used without further purification. MS ESI(+) m/z 445.3 [M+H]+.

Workup

  1. stirringThe reaction was stirred for an additional 20 minutes
  2. waitAfter 10 minutes
  3. customthe cold reaction
  4. customwas quenched by the addition of saturated aqueous ammonium chloride solution (100 mL) and ethyl acetate (100 mL)
  5. temperatureThe reaction was warmed to ambient temperature
  6. customThe layers were separated
  7. extractionthe aqueous layer was extracted with additional ethyl acetate (2×100 mL)
  8. dry with materialThe combined organics were dried with anhydrous Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-c52d23b23f894d6f84116072a65d2e14
Source dataset
uspto-grants-2014_04
Patent number
US08691810B2

Reaction notes

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