HCID 90303368, compound → HCID 90303469, compound

HRID 1051959Notes

Reaction equation

HRID 1051959 reaction equation
[Li]CCCC.[Si:6]([O:13][CH2:14][CH2:15][CH:16]([C:24]1[S:28][C:27](Cl)=[N:26][C:25]=1[Cl:30])[O:17][CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][O:19]1)([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7]>C1COCC1>[Si:6]([O:13][CH2:14][CH2:15][CH:16]([C:24]1[S:28][CH:27]=[N:26][C:25]=1[Cl:30])[O:17][CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][O:19]1)([C:9]([CH3:12])([CH3:10])[CH3:11])([CH3:7])[CH3:8]

Participants

4

Reactant 2

HCID 90303368HCID 90303368, compoundHCID 178418339Butyllithium

Product 1

HCID 90303469HCID 90303469, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

At −78° C., a soln. of n-BuLi in hexanes (2.2 M, 9.6 mL, 21.0 mmol) was added to a soln. of 5-(3-((tert-butyldimethylsilyl)oxy)-1-((tetrahydro-2H-pyran-2-yl)oxy)propyl)-2,4-dichlorothiazole (6.89 g, 16.2 mmol) in THF (125 mL). The mixture was stirred at −78° C. for 45 min, then, quenched by the addition of aq. sat. NaHCO3 and extracted with EtOAc. The comb. org. layers were washed with brine, dried over MgSO4, and conc. in vacuo. Purification by means of CC (2-20% EtOAc/Hept) provided the product as a yellow oil as an isomeric mixture.

Workup

  1. customAt −78° C.
  2. customquenched by the addition of aq. sat. NaHCO3
  3. extractionextracted with EtOAc
  4. washlayers were washed with brine
  5. dry with materialdried over MgSO4
  6. customPurification by means of CC (2-20% EtOAc/Hept)

Sources & evidence

ORD record
ord-6aea3c94e5fc468da0752a45e0a92c88
Source dataset
uspto-grants-2016_07
Patent number
US09388198B2

Reaction notes

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