Sodium Cyanide → Chroman-3-yl-acetonitrile

HRID 984123Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 984123
[O:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH:3]([CH2:11]OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:2]1.[C-:23]#[N:24].[Na+]>CN(C=O)C>[O:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH:3]([CH2:11][C:23]#[N:24])[CH2:2]1

Komponenten

4

Edukt 2

HCID 8929Sodium CyanideHCID 11267124Toluene-4-sulfonic acid Chroman-3-ylmethyl ester

Produkt 1

HCID 14838407Chroman-3-yl-acetonitrileAusbeute 126,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Compound 18B (1.25 g), NaCN (0.15 g) in 25 mL of DMF, were heated to 60° C. for 12 h. The solvent was removed, the reaction mixture was mixed with water (125 mL) and ether (125 mL). The ether layer was separated, washed with water, brine, dried (MgSO4), concentrated to afford compound 18C (0.67 g). mp 54-55.5° C.; MS: 174 (M+1)+. Preparation of 3-Cyanomethyl-chroman-6-sulfonyl chloride (Compound 18D)

Aufarbeitung

  1. customThe solvent was removed
  2. additionthe reaction mixture was mixed with water (125 mL) and ether (125 mL)
  3. customThe ether layer was separated
  4. washwashed with water, brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-b46e117ef1f645828dbbb57f7129736b
Quelldatensatz
uspto-grants-2005_03
Patentnummer
US06867224B2

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