HCID 86761443, compound → HCID 54671156, compound

HRID 561727Notes

Reaction equation

HRID 561727 reaction equation
[F:1][C:2]([F:54])([C:50]([F:53])([F:52])[F:51])[CH2:3][CH2:4][CH2:5][S:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][NH:13][CH2:14][CH2:15][O:16][C:17]1[CH:22]=[CH:21][C:20](/[C:23](/[C:33]2[CH:38]=[CH:37][C:36]([O:39][Si](C(C)C)(C(C)C)C(C)C)=[CH:35][CH:34]=2)=[C:24](\[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)/[CH2:25][CH3:26])=[CH:19][CH:18]=1>C(#N)C>[F:54][C:2]([F:1])([C:50]([F:51])([F:52])[F:53])[CH2:3][CH2:4][CH2:5][S:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][NH:13][CH2:14][CH2:15][O:16][C:17]1[CH:22]=[CH:21][C:20](/[C:23](/[C:33]2[CH:38]=[CH:37][C:36]([OH:39])=[CH:35][CH:34]=2)=[C:24](\[C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)/[CH2:25][CH3:26])=[CH:19][CH:18]=1

Participants

3

Reactant 1

HCID 86761443HCID 86761443, compound

Product 1

HCID 54671156HCID 54671156, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(E)-6-(4,4,5,5,5-pentafluoropentylthio)-N-(2-(4-(2-phenyl-1-(4-(triisopropylsilyloxy)phenyl)but-1-enyl)phenoxy)ethyl)hexan-1-amine from reaction 6 is dissolved in acetonitrile. To this solution is added HF/pyridine complex. The mixture is stirred until the reaction is complete (TLC). When the reaction is complete, the mixture is washed with dilute hydrochloric acid, dilute sodium bicarbonate and water. The aqueous layers are extracted with ethyl acetate. The combined organic extracts are dried over sodium sulfate, filtered, and concentrated under reduced pressure to afford (Z)-4-(1-(4-(2-(6-(4,4,5,5,5-pentafluoropentylthio)hexylamino)ethoxy)phenyl)-2-phenylbut-1-enyl)phenol among other products.

Workup

  1. additionTo this solution is added HF/pyridine complex
  2. washthe mixture is washed with dilute hydrochloric acid, dilute sodium bicarbonate and water
  3. extractionThe aqueous layers are extracted with ethyl acetate
  4. dry with materialThe combined organic extracts are dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3771d5ed50f04aa7986365cb8ac51fff
Source dataset
uspto-grants-2011_11
Patent number
US08063249B1

Reaction notes

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