Tetrabutylammonium Fluoride → HCID 24997809, compound

HRID 2201962Notes

Reaction equation

HRID 2201962 reaction equation
CCCC[N+](CCCC)(CCCC)CCCC.[F-].[CH3:19][O:20][C:21]([C:23]1[S:24][C:25]([CH2:28][CH2:29][CH2:30][C@H:31]2[CH2:35][CH2:34][CH:33]=[C:32]2[C:36]2[CH:41]=[CH:40][C:39]([C@@H:42]([O:48][Si](C(C)(C)C)(C)C)[CH2:43][CH2:44][CH2:45][CH2:46][CH3:47])=[CH:38][CH:37]=2)=[CH:26][CH:27]=1)=[O:22]>[NH4+].[Cl-]>[CH3:19][O:20][C:21]([C:23]1[S:24][C:25]([CH2:28][CH2:29][CH2:30][C@H:31]2[CH2:35][CH2:34][CH:33]=[C:32]2[C:36]2[CH:37]=[CH:38][C:39]([C@@H:42]([OH:48])[CH2:43][CH2:44][CH2:45][CH2:46][CH3:47])=[CH:40][CH:41]=2)=[CH:26][CH:27]=1)=[O:22]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 68706406HCID 68706406, compound

Product 1

HCID 24997809HCID 24997809, compoundYield 73.5%

Reagents, catalysts & solvents 1

HCID 25517Ammonium ChlorideSolvent

Procedure

TBAF (0.4 mL, 0.4 mmol, 1 M/THF) was added to 42b (45 mg, 0.083 mmol) and the resulting solution was allowed to stir for 4 h. Saturated NH4Cl (20 mL) solution was added and the mixture was extracted with ethyl acetate (2×20 mL). The combined ethyl acetate solution was dried (Na2SO4), filtered and evaporated. Purification of the residue by flash chromatography using a Combiflash unit by Teledyne Isco (330 g silica gel, 0%→20% ethyl acetate/hexanes) gave the title compound (26 mg, 0.061 mmol, 73%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate (2×20 mL)
  2. dry with materialThe combined ethyl acetate solution was dried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated
  5. customPurification of the residue by flash chromatography

Sources & evidence

ORD record
ord-4f2505d908124af88dc185789555e751
Source dataset
uspto-grants-2016_06
Patent number
US09365485B2

Reaction notes

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