1,2-Ethanedithiol → 2-Chloro-4-(hydroxymethyl)-3-methylbenzonitrile

HRID 642748

Reaktionsgleichung

Reaktionsgleichung von HRID 642748
[Cl:1][C:2]1[C:3]([CH3:14])=[C:4]([CH:9]=[CH:10][C:11]=1[C:12]#[N:13])[C:5](OC)=[O:6].C(S)CS.[BH4-].[Na+]>C1COCC1>[Cl:1][C:2]1[C:3]([CH3:14])=[C:4]([CH2:5][OH:6])[CH:9]=[CH:10][C:11]=1[C:12]#[N:13]

Komponenten

5

Edukt 3

HCID 109021,2-EthanedithiolHCID 4311764Sodium borohydrideHCID 68579417Methyl 3-chloro-4-cyano-2-methylbenzoate

Produkt 1

HCID 685775712-Chloro-4-(hydroxymethyl)-3-methylbenzonitrileAusbeute 66,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To a pressure reaction flask containing compound 7A (1.5 g, 7.2 mmol) in THF (30 mL) were added 1,2-ethanedithiol (2.4 g, 28.6 mmol) and NaBH4 (812 mg, 21.5 mmol). It was sealed, and heated at 70° C. for 2 hr, and cooled to RT. The reaction mixture was concentrated, dissolved in EtOAc, washed with water, dried over Na2SO4, and concentrated. Recrystallization in EtOAc/hexanes give the title compound (870 mg). (ES) m/z 182 [M+H]+; 204 [M+Na]+.

Aufarbeitung

  1. customTo a pressure reaction flask
  2. customIt was sealed
  3. temperaturecooled to RT
  4. concentrationThe reaction mixture was concentrated
  5. dissolutiondissolved in EtOAc
  6. washwashed with water
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated
  9. customRecrystallization in EtOAc/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-6f973348b7b245bc91aa790a6ac3c759
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07696241B2

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