Tetrabutylammonium Fluoride → HCID 90303201, compound

HRID 1051925Notes

Reaction equation

HRID 1051925 reaction equation
CCCC[N+](CCCC)(CCCC)CCCC.[F-].[Si]([O:26][CH2:27][CH2:28][CH:29]([C:37]1[S:41][CH:40]=[N:39][C:38]=1[Cl:42])[O:30][CH:31]1[CH2:36][CH2:35][CH2:34][CH2:33][O:32]1)(C(C)(C)C)(C)C>C1COCC1>[Cl:42][C:38]1[N:39]=[CH:40][S:41][C:37]=1[CH:29]([O:30][CH:31]1[CH2:36][CH2:35][CH2:34][CH2:33][O:32]1)[CH2:28][CH2:27][OH:26]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 90303469HCID 90303469, compound

Product 1

HCID 90303201HCID 90303201, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

At 0° C., a soln. of TBAF in THF (1 M, 19.2 mL, 19.2 mmol) was added to a. soln. of 5-(3-((tert-butyldimethylsilyl)oxy)-1-((tetrahydro-2H-pyran-2-yl)oxy)propyl)-4-chlorothiazole (6.27 g, 16.0 mmol) in THF (80 mL). The mixture was allowed to warm to RT and stirred overnight. Then, the mixture was 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 (20-85% EtOAc/Hept) provided the product as a yellow oil as an isomeric mixture.

Workup

  1. customAt 0° C.
  2. customThen, the mixture was quenched 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 (20-85% EtOAc/Hept)

Sources & evidence

ORD record
ord-9e687102bf2d49c1846cebff0e7c9948
Source dataset
uspto-grants-2016_07
Patent number
US09388197B2

Reaction notes

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