Hexafluoroacetone → (e)-6-{5-[3,4-Bis(tert-butyldimethylsilanyloxy-methyl)phenoxymethyl]-2-thienyl}-1,1,1-trifluoro-2-trifluoromethyloct-5-en-3-yn-2-ol

HRID 49365

Reaktionsgleichung

Reaktionsgleichung von HRID 49365
[Si:1]([O:8][CH2:9][C:10]1[CH:11]=[C:12]([CH:26]=[CH:27][C:28]=1[CH2:29][O:30][Si:31]([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:33])[CH3:32])[O:13][CH2:14][C:15]1[S:16][C:17](/[C:20](/[CH2:24][CH3:25])=[CH:21]/[C:22]#[CH:23])=[CH:18][CH:19]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C([Li])CCC.[F:43][C:44]([F:52])([F:51])[C:45]([C:47]([F:50])([F:49])[F:48])=[O:46]>C1COCC1>[Si:1]([O:8][CH2:9][C:10]1[CH:11]=[C:12]([CH:26]=[CH:27][C:28]=1[CH2:29][O:30][Si:31]([C:34]([CH3:36])([CH3:35])[CH3:37])([CH3:32])[CH3:33])[O:13][CH2:14][C:15]1[S:16][C:17](/[C:20](/[CH2:24][CH3:25])=[CH:21]/[C:22]#[C:23][C:45]([C:47]([F:50])([F:49])[F:48])([OH:46])[C:44]([F:52])([F:51])[F:43])=[CH:18][CH:19]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 12695HexafluoroacetoneHCID 880121392-[3,4-bis(tert-butyldimethylsilanyloxymethyl)phenoxymethyl]-5-((E)-1-ethyl-but-1-en-3-ynyl)thiopheneHCID 178418339Butyllithium

Produkt 1

HCID 20636349(e)-6-{5-[3,4-Bis(tert-butyldimethylsilanyloxy-methyl)phenoxymethyl]-2-thienyl}-1,1,1-trifluoro-2-trifluoromethyloct-5-en-3-yn-2-ol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

1.7 g (3 mmol) of 2-[3,4-bis(tert-butyldimethylsilanyloxymethyl)phenoxymethyl]-5-((E)-1-ethyl-but-1-en-3-ynyl)thiophene are dissolved in 50 mL of THF and the mixture is cooled to −78° C. 1.3 mL (3.3 mmol) of 2.5 M butyllithium are then added. After stirring for 15 minutes at the same temperature, a gentle flow of hexafluoroacetone (gas) is introduced into the reaction medium. After reaction for 20 minutes at −78° C., the flow of gas is stopped and the reaction medium is treated in the usual manner. The residue obtained is purified by chromatography on silica gel. The desired product is obtained in the form of a yellow oil (1 g).

Aufarbeitung

  1. customAfter reaction for 20 minutes at −78° C.
  2. additionthe reaction medium is treated in the usual manner
  3. customThe residue obtained
  4. customis purified by chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-22abab40fc7b49eeb1a7d05376d358b9
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06706725B1

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