Methanol → HCID 86647826, Verbindung

HRID 241071Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 241071
[Cl:1][C:2]1[C:11]2[CH2:10][CH2:9][CH:8]([CH:12]=C)[CH2:7][C:6]=2[N:5]=[CH:4][N:3]=1.[BH4-].[Na+].C[OH:17]>ClCCl>[Cl:1][C:2]1[C:11]2[CH2:10][CH2:9][CH:8]([CH2:12][OH:17])[CH2:7][C:6]=2[N:5]=[CH:4][N:3]=1

Komponenten

5

Edukt 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 866478274-Chloro-7-vinyl-5,6,7,8-tetrahydroquinazoline

Produkt 1

HCID 86647826HCID 86647826, VerbindungAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Ozone was bubbled through a cooled (−78° C.) solution of 4-chloro-7-vinyl-5,6,7,8-tetrahydroquinazoline (reagent preparation 3, 0.35 g, 1.8 mmol) in methanol (5 mL) and dichloromethane (30 mL) until a blue color persisted. The solution was then sparged with N2 for 10 minutes and sodium borohydride (0.14 g, 3.6 mmol) was added portionwise. After 30 minutes the reaction mixture was partitioned between dichloromethane and saturated aqueous sodium bicarbonate. The organic layer was washed with brine, dried over magnesium sulfate, filtered and then concentrated in vacuo to provide (4-chloro-5,6,7,8-tetrahydroquinazolin-7-yl)methanol (0.32 g, 90% yield) as a waxy solid. MS (ES) for C9H11ClN2O: 199 (MH+).

Aufarbeitung

  1. customOzone was bubbled through
  2. customThe solution was then sparged with N2 for 10 minutes
  3. customAfter 30 minutes the reaction mixture was partitioned between dichloromethane and saturated aqueous sodium bicarbonate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-1ae047abe0194348bcddfb7caba16665
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08648066B2

Notizen zur Reaktion

Wird geladen…