Dimethylformamide → 7-(1-Adamantyl)-6-tert-butyldimethylsilyloxy-2-bromonaphthalene

HRID 1143

Reaktionsgleichung

Reaktionsgleichung von HRID 1143
[C:1]12([C:11]3[CH:20]=[C:19]4[C:14]([CH:15]=[CH:16][C:17]([Br:21])=[CH:18]4)=[CH:13][C:12]=3[OH:22])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.CN(C=O)C.C(N(CC)CC)C.[Si:35](Cl)([C:38]([CH3:41])([CH3:40])[CH3:39])([CH3:37])[CH3:36]>CN(C)C1C=CN=CC=1.O>[C:1]12([C:11]3[CH:20]=[C:19]4[C:14]([CH:15]=[CH:16][C:17]([Br:21])=[CH:18]4)=[CH:13][C:12]=3[O:22][Si:35]([C:38]([CH3:41])([CH3:40])[CH3:39])([CH3:37])[CH3:36])[CH2:8][CH:7]3[CH2:9][CH:3]([CH2:4][CH:5]([CH2:6]3)[CH2:10]1)[CH2:2]2

Komponenten

7

Edukt 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 145490723-(Adamantan-1-yl)-6-bromonaphthalen-2-ol

Produkt 1

HCID 196946817-(1-Adamantyl)-6-tert-butyldimethylsilyloxy-2-bromonaphthalene

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

11.9 g (33.3 mmol) of 7-(1-adamantyl)-6-hydroxy-2-bromonaphthalene, 120 ml of DMF, 5.1 ml (36.6 mmol) of triethylamine and 203 mg of 4-dimethylaminopyridine were introduced successively into a three-necked flask. A solution of 5.52 g (36.6 mmol) of tert-butyldimethylsilyl chloride was added dropwise and the mixture was stirred at room temperature for 12 hours. The reaction medium was poured into water, extracted with ethyl ether, the organic phase decanted, dried over magnesium sulfate and evaporated. The residue obtained was purified by chromatography on a silica column eluted with heptane; 12 g (76%) of 7-(1-adamantyl)-6-tert-butyldimethylsilyloxy-2-bromonaphthalene of melting point 120°-121° C. were recovered.

Aufarbeitung

  1. extractionextracted with ethyl ether
  2. customthe organic phase decanted
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customThe residue obtained
  6. customwas purified by chromatography on a silica column
  7. washeluted with heptane
  8. custom12 g (76%) of 7-(1-adamantyl)-6-tert-butyldimethylsilyloxy-2-bromonaphthalene of melting point 120°-121° C. were recovered

Quellen und Nachweise

ORD-Eintrag
ord-a18ffbdb8f6b474a86827045ded0ce46
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05723499

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