Hydrochloric Acid → (S)-(+)-3-Cyano-4-(2-methylbutyloxy)phenylboronic acid

HRID 442586Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 442586
[Li].[C:2]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[O:13][CH2:14][C@@H:15]([CH3:18])[CH2:16][CH3:17])C(O)=O)#[N:3].[B:19](OC)([O:22]C)[O:20]C.Cl>C1COCC1>[C:2]([C:4]1[CH:5]=[C:6]([B:19]([OH:22])[OH:20])[CH:10]=[CH:11][C:12]=1[O:13][CH2:14][C@@H:15]([CH3:18])[CH2:16][CH3:17])#[N:3]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 8470Trimethyl borateHCID 3028194Lithium2×HCID 54501986(S)-(+)-3-Cyano-4-(2-methylbutyloxy)benzoic acid

Produkt 1

HCID 53923893(S)-(+)-3-Cyano-4-(2-methylbutyloxy)phenylboronic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

The experimental procedure for the preparation of the lithium salt was as described in the preparation of compound 43. A solution of trimethyl borate (2.70 g, 0.024 mol) in dry THF (10 ml) was added dropwise to the lithium salt solution. The resultant mixture was allowed to warm to room temperature overnight whilst stirring and dilute hydrochloric acid was then added. The THF/water azeotrope was removed in vacuo and the remaining residue was dissolved in diethyl ether and washed with water until acid-free. The ether was dried (MgSO4) and removed in vacuo to leave a fawn solid.

Aufarbeitung

  1. customThe THF/water azeotrope was removed in vacuo
  2. dissolutionthe remaining residue was dissolved in diethyl ether
  3. washwashed with water until acid-free
  4. dry with materialThe ether was dried (MgSO4)
  5. customremoved in vacuo
  6. customto leave a fawn solid

Quellen und Nachweise

ORD-Eintrag
ord-8d36b30d02454af9b5c685ec55fb20d7
Quelldatensatz
uspto-grants-1999_04
Patentnummer
US05891358

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