Tetrabutylammonium Fluoride → HCID 59710626, compound

HRID 2221130Notes

Reaction equation

HRID 2221130 reaction equation
[C:1]([S:20][CH2:21][CH2:22][O:23][CH2:24][CH2:25][O:26][CH2:27][CH2:28][O:29][CH2:30][CH2:31]OS(C)(=O)=O)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F-:37].C([N+](CCCC)(CCCC)CCCC)CCC>>[F:37][CH2:31][CH2:30][O:29][CH2:28][CH2:27][O:26][CH2:25][CH2:24][O:23][CH2:22][CH2:21][S:20][C:1]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 59710632HCID 59710632, compound

Product 1

HCID 59710626HCID 59710626, compoundYield 71%

Procedure

A stirring solution of methanesulfonic acid 2-{2-[2-(2-tritylsulfanyl-ethoxy)-ethoxy]-ethoxy}-ethyl ester (71.67 mg, 0.14 mmol) and tetrabutylammonium fluoride (1.1 M in THF, 127 μl, 0.14 mmol) was heated at 90° C. for 30 minutes. The mixture was cooled to ambient temperature and evaporated to dryness. Purification of product was by flash chromatography using ethyl acetate/hexane, (1:1) to give the product (71%) as a colourless oil.

Workup

  1. customevaporated to dryness
  2. customPurification of product

Sources & evidence

ORD record
ord-53c7487a69044569b62d605987def3ad
Source dataset
uspto-grants-2008_05
Patent number
US07368474B2

Reaction notes

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