Chloroacetaldehyde → HCID 59150497, Verbindung

HRID 1668571Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1668571
[CH3:1][C:2]1[O:3][C:4]2[C:14]([N:15]=1)=[CH:13][C:7]1[CH2:8][CH2:9][NH:10][CH2:11][CH2:12][C:6]=1[CH:5]=2.[Cl:16][CH2:17][CH:18]=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>COCCOC>[Cl:16][CH2:17][CH2:18][N:10]1[CH2:9][CH2:8][C:7]2[CH:13]=[C:14]3[N:15]=[C:2]([CH3:1])[O:3][C:4]3=[CH:5][C:6]=2[CH2:12][CH2:11]1

Komponenten

5

Edukt 3

HCID 33ChloroacetaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 591504802-Methyl-6,7,8,9-tetrahydro-5H-[1,3]oxazolo[4,5-h][3]benzazepine

Produkt 1

HCID 59150497HCID 59150497, VerbindungAusbeute 36 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

A mixture 2-methyl-6,7,8,9-tetrahydro-5H-[1,3]oxazolo[4,5-h][3]benzazepine (1 mmol), chloroacetaldehyde (2 mmol), NaBH(OAc)3 (2 mmol) in dry DME (10 ml) was stirred at room temperature for 3 h. The mixture was partitioned between aqueous Na2CO3 (0.5 M) and DCM. The organic layer was collected and the aqueous phase extracted twice with DCM. The combined DCM layers were concentrated and submitted to column chromatography (EtOAc—acetone gradient) to provide the title compound (36% yield).

Aufarbeitung

  1. customThe mixture was partitioned between aqueous Na2CO3 (0.5 M) and DCM
  2. customThe organic layer was collected
  3. extractionthe aqueous phase extracted twice with DCM
  4. concentrationThe combined DCM layers were concentrated

Quellen und Nachweise

ORD-Eintrag
ord-752220f6d3f94ed3ba7be2505ff68da7
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US07989444B2

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