Hydrochloric Acid → 7-(1-Adamantyl)-6-benzyloxy-2-naphthylboronic acid

HRID 618480Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 618480
[C:1]12([C:11]3[CH:20]=[C:19]4[C:14]([CH:15]=[CH:16][C:17](Br)=[CH:18]4)=[CH:13][C:12]=3[O:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.C([Li])CCC.[B:35](OC)([O:38]C)[O:36]C.Cl>C1COCC1>[C:1]12([C:11]3[CH:20]=[C:19]4[C:14]([CH:15]=[CH:16][C:17]([B:35]([OH:38])[OH:36])=[CH:18]4)=[CH:13][C:12]=3[O:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 8470Trimethyl borateHCID 220003597-(1-Adamantyl)-6-benzyloxy-2-bromonaphthaleneHCID 178418339Butyllithium

Produkt 1

HCID 220003137-(1-Adamantyl)-6-benzyloxy-2-naphthylboronic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

3 g (6.7 mmol) of 7-(1-adamantyl)-6-benzyloxy-2-bromonaphthalene and 50 ml of THF were introduced into a three-necked flask under a stream of nitrogen. 3.2 ml (8 mmol) of n-butyllithium (2.5M in hexane) were added dropwise at -78° C. and stirring was carried out for 15 minutes, at the same temperature. 2.1 g (20 mmol) of trimethyl borate were added and stirring was carried out for 2 hours. 23 ml of hydrochloric acid (1N) were added at -50° C. and the temperature was permitted to increase to room temperature. The reaction mixture was extracted with ethyl ether and the organic phase was separated by settling, dried over magnesium sulfate and evaporated. The residue obtained was triturated in heptane, filtered and dried. 2.8 g (100%) of the expected boronic acid were collected, which acid was used, as is, in the synthesis to follow.

Aufarbeitung

  1. stirringstirring
  2. waitwas carried out for 2 hours
  3. extractionThe reaction mixture was extracted with ethyl ether
  4. customthe organic phase was separated
  5. dry with materialdried over magnesium sulfate
  6. customevaporated
  7. customThe residue obtained
  8. customwas triturated in heptane
  9. filtrationfiltered
  10. customdried
  11. custom2.8 g (100%) of the expected boronic acid were collected
  12. customas is, in the synthesis

Quellen und Nachweise

ORD-Eintrag
ord-f8f190b771e24f069e6cd5ea28924037
Quelldatensatz
uspto-grants-1999_09
Patentnummer
US05952382

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