Hexane → HCID 23028708, Verbindung

HRID 748676

Reaktionsgleichung

Reaktionsgleichung von HRID 748676
C([Li])CCC.CCCCCC.[Si:12]([O:19][CH2:20][CH2:21][CH2:22][CH2:23][CH:24]([C:35]1[CH:40]=[C:39]([F:41])[CH:38]=[CH:37][C:36]=1[F:42])[S:25]([C:28]1[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=1)(=[O:27])=[O:26])([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13].[Si:43]([O:50][CH2:51][CH2:52][CH2:53][CH2:54]I)([C:46]([CH3:49])([CH3:48])[CH3:47])([CH3:45])[CH3:44]>O.O1CCCC1>[Si:12]([O:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]([C:35]1[CH:40]=[C:39]([F:41])[CH:38]=[CH:37][C:36]=1[F:42])([CH2:54][CH2:53][CH2:52][CH2:51][O:50][Si:43]([C:46]([CH3:47])([CH3:49])[CH3:48])([CH3:44])[CH3:45])[S:25]([C:28]1[CH:29]=[CH:30][C:31]([Cl:34])=[CH:32][CH:33]=1)(=[O:27])=[O:26])([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13]

Komponenten

7

Edukt 4

HCID 8058HexaneHCID 4250746tert-Butyl(4-iodobutoxy)dimethylsilaneHCID 59750776HCID 59750776, VerbindungHCID 178418339Butyllithium

Produkt 1

HCID 23028708HCID 23028708, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

In an argon gas stream and at −78° C., n-butyl lithium (a 1.57M hexane solution, 0.358 ml, 0.562 mmol) was added to a tetrahydrofuran (4 ml) solution of the 2-[5-(t-butyldimethylsilyloxy)-1-[(4-chlorophenyl)sulfonyl]pentyl]-1,4-difluorobenzene (250 mg, 0.511 mmol) obtained in Example 15. The temperature of the resulting mixture was raised to room temperature. After cooling to −78° C., 4-(t-butyldimethylsilyloxy)-1-iodobutane (0.146 ml, 0.562 mmol) was added dropwise to the reaction mixture. The reaction mixture was stirred at room temperature for 3 days. Water was added to the reaction mixture, followed by extraction with diethyl ether. The extracts were combined, washed successively with water and brine, dried over MgSO4, and then concentrated. The residue thus obtained was purified by medium-pressure chromatography on a silica gel column (6% ethyl acetate-hexane), whereby the title compound (167 mg, 48%) was obtained as a colorless solid.

Aufarbeitung

  1. temperatureAfter cooling to −78° C.
  2. extractionfollowed by extraction with diethyl ether
  3. washwashed successively with water and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe residue thus obtained
  7. customwas purified by medium-pressure chromatography on a silica gel column (6% ethyl acetate-hexane), whereby the title compound (167 mg, 48%)
  8. customwas obtained as a colorless solid

Quellen und Nachweise

ORD-Eintrag
ord-d7cd4b9d3d83465c8cd14af07dfb58f8
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07399775B2

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