Tetrahydrofuran → HCID 59300229, compound

HRID 2236548Notes

Reaction equation

HRID 2236548 reaction equation
[CH2:1]([O:8][C:9]1[C:14]([O:15][CH2:16][CH2:17][CH3:18])=[CH:13][CH:12]=[C:11]([CH2:19][O:20][Si](C(C)C)(C(C)C)C(C)C)[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1>O>[CH2:1]([O:8][C:9]1[N:10]=[C:11]([CH2:19][OH:20])[CH:12]=[CH:13][C:14]=1[O:15][CH2:16][CH2:17][CH3:18])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 2724141Tetrabutylammonium FluorideHCID 59300056HCID 59300056, compound

Product 1

HCID 59300229HCID 59300229, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 2-benzyloxy-3-propoxy-6-triisopropylsilanyloxymethyl-pyridine (860 mg, 2.0 mmole) is added 1M tetrabutylammonium fluoride solution in tetrahydrofuran (4.0 mL, 4.0 mmole) and the mixture stirred at room temperature for four hours. The reaction mixture is diluted with water and extracted with ether. The combined ether layers were combined and washed with water, dried over sodium sulfate, filtered, chromatographed on silica gel eluting with 1:1 hexanes/ether to give a white solid, 355 mg, (65%); m.p. 50-1° C., MS (ES+): m/z 274.1 (M+H).

Workup

  1. extractionextracted with ether
  2. washwashed with water
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customchromatographed on silica gel eluting with 1:1 hexanes/ether
  6. customto give a white solid, 355 mg, (65%)

Sources & evidence

ORD record
ord-beffff42d2234823998776881388da03
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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