Tetrahydrofuran → HCID 57709092, compound

HRID 546978Notes

Reaction equation

HRID 546978 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1.[CH3:24][O:25][C:26](=[O:67])[CH2:27][C:28]1[CH:33]=[CH:32][C:31]([C:34]2[CH:39]=[CH:38][C:37]([C:40]([CH2:63][CH3:64])([C:43]3[CH:48]=[CH:47][C:46]([C:49]#[C:50][C:51]4([O:57][Si](C)(C)C)[CH2:56][CH2:55][CH2:54][CH2:53][CH2:52]4)=[C:45]([CH3:62])[CH:44]=3)[CH2:41][CH3:42])=[CH:36][C:35]=2[CH3:65])=[CH:30][C:29]=1[F:66].[Cl-].[NH4+]>>[CH3:24][O:25][C:26](=[O:67])[CH2:27][C:28]1[CH:33]=[CH:32][C:31]([C:34]2[CH:39]=[CH:38][C:37]([C:40]([CH2:63][CH3:64])([C:43]3[CH:48]=[CH:47][C:46]([C:49]#[C:50][C:51]4([OH:57])[CH2:56][CH2:55][CH2:54][CH2:53][CH2:52]4)=[C:45]([CH3:62])[CH:44]=3)[CH2:41][CH3:42])=[CH:36][C:35]=2[CH3:65])=[CH:30][C:29]=1[F:66]

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 2724141Tetrabutylammonium FluorideHCID 57709058HCID 57709058, compound

Product 1

HCID 57709092HCID 57709092, compoundYield 92.8%

Procedure

A 1 M solution of tetrabutylammonium fluoride in tetrahydrofuran (0.105 mL, 0.105 mmol) was added to (4′-{1-ethyl-1-[3-methyl-4-(1-trimethylsilanyloxy-cyclohexylethynyl)-phenyl]-propyl}-3-fluoro-2′-methyl-biphenyl-4-yl)acetic acid methyl ester (Example 97-(1); 54.0 mg, 0.0881 mmol), and the mixture was stirred for 40 minutes. A saturated aqueous ammonium chloride solution was added to the reaction mixture, followed by extraction with diethyl ether. The organic layer was washed with water, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography (20% ethyl acetate/hexane) to give the title compound (44.2 mg, 92%).

Workup

  1. extractionfollowed by extraction with diethyl ether
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel chromatography (20% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-2b095bdb658f4ea7a96c271d89e800b8
Source dataset
uspto-grants-2011_05
Patent number
US07935688B2

Reaction notes

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