Sodium Chloride → HCID 53982091, compound

HRID 1419634Notes

Reaction equation

HRID 1419634 reaction equation
[CH2:1]([O:3][CH:4]([O:6][C@H:7]1[CH2:12][C@H:11]([O:13][CH:14]([O:16][CH2:17][CH3:18])[CH3:15])[CH2:10][CH:9]([O:19][Si](C(C)(C)C)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:8]1[CH3:37])[CH3:5])[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Cl-].[Na+]>C1COCC1>[CH2:1]([O:3][CH:4]([O:6][C@H:7]1[CH2:12][C@H:11]([O:13][CH:14]([O:16][CH2:17][CH3:18])[CH3:15])[CH2:10][CH:9]([OH:19])[CH:8]1[CH3:37])[CH3:5])[CH3:2]

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 2724141Tetrabutylammonium FluorideHCID 21308560HCID 21308560, compound

Product 1

HCID 53982091HCID 53982091, compoundYield 68.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

6.48 g (12.14 mmol) of 18 and 6.31 g (20 mmol) of tetrabutylammonium fluoride (hydrate) in 150 ml of THF is stirred overnight at room temperature. Then, it is hydrolyzed with sodium chloride solution, extracted with ethyl acetate, washed with sodium chloride solution and dried on sodium sulfate. After concentration by evaporation, the residue is chromatographed on silica gel (mobile solvent: EE:H=8:2), whereby 2.41 g (8.3 mmol) of title compound 19 is obtained.

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with sodium chloride solution
  3. customdried on sodium sulfate
  4. concentrationAfter concentration
  5. customby evaporation
  6. customthe residue is chromatographed on silica gel (mobile solvent: EE:H=8:2)

Sources & evidence

ORD record
ord-2242da7c378845d2827cf58ff0174ad2
Source dataset
uspto-grants-1999_03
Patent number
US05886233

Reaction notes

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