Water → HCID 70162721, compound

HRID 844426Notes

Reaction equation

HRID 844426 reaction equation
C([Li])CCC.[CH3:6][C:7]1[N:8]([C:13]2[S:14][CH:15]=[C:16]([C:18]3[C:23]([O:24][CH3:25])=[CH:22][C:21]([CH3:26])=[CH:20][C:19]=3[O:27][CH3:28])[N:17]=2)[C:9]([CH3:12])=[CH:10][CH:11]=1.S(O[CH:37]([CH:39]1[CH2:44][CH2:43][CH2:42][CH2:41][CH2:40]1)[CH3:38])(C(F)(F)F)(=O)=O.O>CCCCCC>[CH:39]1([CH2:37][CH2:38][C:15]2[S:14][C:13]([N:8]3[C:7]([CH3:6])=[CH:11][CH:10]=[C:9]3[CH3:12])=[N:17][C:16]=2[C:18]2[C:23]([O:24][CH3:25])=[CH:22][C:21]([CH3:26])=[CH:20][C:19]=2[O:27][CH3:28])[CH2:44][CH2:43][CH2:42][CH2:41][CH2:40]1

Participants

6

Reactant 4

HCID 962WaterHCID 57114752HCID 57114752, compoundHCID 87266712HCID 87266712, compoundHCID 178418339Butyllithium

Product 1

HCID 70162721HCID 70162721, compoundYield 9.1%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
-30 °C

Procedure

10 ml of 1.6M n-butyllithium in hexane are added, at −30° C., to 4.27 g of 2-(2,5-dimethylpyrrol-1-yl)-4-(2,6-dimethoxy-4-methylphenyl) thiazole and the mixture is left stirring for 30 minutes at −30° C. 4.2 g of cyclohexylethanol triflate are added at −45° C., the mixture is then warmed to 0° C., water is added, this mixture is extracted with Et2O and the extracts are dried and evaporated. The gum formed is chromatographed on silica, eluting with cyclohexane/EtOAc (1/1; v/v). 0.52 g of the expected compound is obtained in the form of a colourless gum.

Workup

  1. waitthe mixture is left
  2. temperaturethe mixture is then warmed to 0° C.
  3. extractionthis mixture is extracted with Et2O
  4. customthe extracts are dried
  5. customevaporated
  6. customThe gum formed
  7. customis chromatographed on silica
  8. washeluting with cyclohexane/EtOAc (1/1; v/v)

Sources & evidence

ORD record
ord-41696f0c41e7411eba0ced8785ce4cff
Source dataset
uspto-grants-2002_04
Patent number
US06380230B1

Reaction notes

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