Tetrabutylammonium Fluoride → HCID 66693020, compound

HRID 1469192Notes

Reaction equation

HRID 1469192 reaction equation
[Cl:1][C:2]1[S:3][C:4]([CH:19]2[C@H:24]([O:25][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C@@H:23]([O:33][CH2:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[C@H:22]([O:41][CH2:42][C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)[C@@H:21]([CH2:49][O:50][CH2:51][C:52]3[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=3)[O:20]2)=[CH:5][C:6]=1[CH2:7][O:8][Si](C(C)C)(C(C)C)C(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[Cl:1][C:2]1[S:3][C:4]([CH:19]2[C@H:24]([O:25][CH2:26][C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[C@@H:23]([O:33][CH2:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[C@H:22]([O:41][CH2:42][C:43]3[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=3)[C@@H:21]([CH2:49][O:50][CH2:51][C:52]3[CH:53]=[CH:54][CH:55]=[CH:56][CH:57]=3)[O:20]2)=[CH:5][C:6]=1[CH2:7][OH:8]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 66691356HCID 66691356, compound

Product 1

HCID 66693020HCID 66693020, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of compound 34 (8.22 g) in THF (50 mL) was added TBAF (1M in THF, 20 mL, 19.9 mmol) dropwise at 0° C. The mixture was stirred at room temperature for 2 hours. The mixture was extracted with EtOAc/H2O (100 mL/250 mL). The organic layer was dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by silica column chromatography (Biotage) to provide the title compound 35 (5.2 g, 89% (3-steps)).

Workup

  1. extractionThe mixture was extracted with EtOAc/H2O (100 mL/250 mL)
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica column chromatography (Biotage)

Sources & evidence

ORD record
ord-f0d410af4e8c4852a769e189ea87b947
Source dataset
uspto-grants-2015_04
Patent number
US09006187B2

Reaction notes

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