3-[2-Benzyloxy-4-(1,1-dimethylheptyl)phenyl]-1-dibromomethyl-4,5-dimethylcyclohexanol → 3-[2-Benzyloxy-4-(1,1-dimethylheptyl)phenyl]-4,5-dimethylcycloheptanone

HRID 1660072Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1660072
C([O:8][C:9]1[CH:14]=[C:13]([C:15]([CH3:23])([CH3:22])[CH2:16][CH2:17][CH2:18]CCC)[CH:12]=[CH:11][C:10]=1[CH:24]1[CH:29]([CH3:30])[CH:28]([CH3:31])[CH2:27][C:26]([CH:33](Br)Br)([OH:32])[CH2:25]1)C1C=CC=CC=1.[CH2:36]([Li])[CH2:37][CH2:38][CH3:39]>O1CCCC1>[CH2:36]([O:8][C:9]1[CH:14]=[C:13]([C:15]([CH3:23])([CH3:22])[CH2:16][CH2:17][CH2:18][CH2:11][CH2:12][CH3:13])[CH:12]=[CH:11][C:10]=1[CH:24]1[CH:29]([CH3:30])[CH:28]([CH3:31])[CH2:27][CH2:33][C:26](=[O:32])[CH2:25]1)[C:37]1[CH:14]=[CH:9][CH:10]=[CH:39][CH:38]=1

Komponenten

4

Edukt 2

HCID 204969043-[2-Benzyloxy-4-(1,1-dimethylheptyl)phenyl]-1-dibromomethyl-4,5-dimethylcyclohexanolHCID 178418339Butyllithium

Produkt 1

HCID 204968973-[2-Benzyloxy-4-(1,1-dimethylheptyl)phenyl]-4,5-dimethylcycloheptanone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a -78° C. solution of 30.4 g (0.050 mole) of 3-[2-benzyloxy-4-(1,1-dimethylheptyl)phenyl]-1-dibromomethyl-4,5-dimethylcyclohexanol in 150 ml of tetrahydrofuran is slowly added over a period of 2 hours 47.7 ml (0.105 mole) of n-butyllithium (2.2 M in hexane). The reaction solution is stirred 2 hours longer at -78° C. and 10 minutes at 0° C. and then quenched by pouring into 300 ml of ice cold 1 N hydrochloric acid. The quenched reaction is extracted with two 250 ml portions of ether, the combined extract washed with 250 ml of saturated sodium chloride, dried over magnesium sulfate and evaporated. The residue is purified via column chromatography on 500 g of silica gel eluted with ether-pentane to yield the title compound.

Aufarbeitung

  1. customquenched
  2. additionby pouring into 300 ml of ice cold 1 N hydrochloric acid
  3. customThe quenched reaction
  4. extractionis extracted with two 250 ml portions of ether
  5. extractionthe combined extract
  6. washwashed with 250 ml of saturated sodium chloride
  7. dry with materialdried over magnesium sulfate
  8. customevaporated
  9. customThe residue is purified via column chromatography on 500 g of silica gel
  10. washeluted with ether-pentane

Quellen und Nachweise

ORD-Eintrag
ord-d2d0480ac9e1478db4a908690e041fb4
Quelldatensatz
uspto-grants-1981_12
Patentnummer
US04306097

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