Tetrabutylammonium Fluoride → HCID 57709019, compound

HRID 546821Notes

Reaction equation

HRID 546821 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C[O:20][C:21](=[O:64])[CH2:22][CH2:23][C:24]1[CH:25]=[C:26]([C:30]2[CH:35]=[CH:34][C:33]([C:36]([C:41]3[CH:46]=[CH:45][C:44]([CH2:47][CH2:48][CH:49]([O:54][Si](C(C)(C)C)(C)C)[C:50]([CH3:53])([CH3:52])[CH3:51])=[C:43]([CH3:62])[CH:42]=3)([CH2:39][CH3:40])[CH2:37][CH3:38])=[CH:32][C:31]=2[CH3:63])[CH:27]=[CH:28][CH:29]=1.P([O-])(O)(O)=O.[Na+]>O1CCCC1>[CH2:37]([C:36]([C:33]1[CH:34]=[CH:35][C:30]([C:26]2[CH:27]=[CH:28][CH:29]=[C:24]([CH2:23][CH2:22][C:21]([OH:64])=[O:20])[CH:25]=2)=[C:31]([CH3:63])[CH:32]=1)([C:41]1[CH:46]=[CH:45][C:44]([CH2:47][CH2:48][CH:49]([OH:54])[C:50]([CH3:52])([CH3:53])[CH3:51])=[C:43]([CH3:62])[CH:42]=1)[CH2:39][CH3:40])[CH3:38]

Participants

5

Reactant 3

HCID 2724141Tetrabutylammonium FluorideHCID 23672064Monosodium phosphateHCID 57708913HCID 57708913, compound

Product 1

HCID 57709019HCID 57709019, compoundYield 93.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

Tetra-n-butylammonium fluoride (1 M solution in tetrahydrofuran, 0.2 mL, 0.2 mmol) and tetrahydrofuran (1 mL) were added to 3-[4′-(1-{4-[3-(t-butyl-dimethyl-silanyloxy)-4,4-dimethyl-pentyl]-3-methyl-phenyl}-1-ethyl-propyl)-2′-methyl-biphenyl-3-yl]-propionic acid methyl ester (Example 12-(2); 0.016 g, 0.025 mmol), and the mixture was stirred at 60° C. for four hours. A 30% sodium dihydrogenphosphate aqueous solution was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by preparative TLC (hexane/ethyl acetate=1/1) to give the title compound (0.012 g, 93%).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by preparative TLC (hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-e752a7b9470f49cf8ed272293bf82e2b
Source dataset
uspto-grants-2011_05
Patent number
US07935688B2

Reaction notes

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