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4-Chlorobenzoyl chloride → tert-Butyl 2-(4-(3-(4-chlorophenyl)-3-oxopropanoyl)phenyl)morpholine-4-carboxylate

HRID 710237
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 710237
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[O:15][CH2:14][CH2:13][N:12]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:11]2)=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[Li].C[Si]([N-][Si](C)(C)C)(C)C.[Cl:33][C:34]1[CH:42]=[CH:41][C:37]([C:38](Cl)=[O:39])=[CH:36][CH:35]=1>C1COCC1>[Cl:33][C:34]1[CH:42]=[CH:41][C:37]([C:38](=[O:39])[CH2:2][C:1]([C:4]2[CH:5]=[CH:6][C:7]([CH:10]3[O:15][CH2:14][CH2:13][N:12]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:11]3)=[CH:8][CH:9]=2)=[O:3])=[CH:36][CH:35]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 85014-Chlorobenzoyl chlorideHCID 86605622Lithium bistrimethylsilylamideHCID 89689432tert-Butyl 2-(4-acetylphenyl)morpholine-4-carboxylate

Produkt 1

HCID 89689396tert-Butyl 2-(4-(3-(4-chlorophenyl)-3-oxopropanoyl)phenyl)morpholine-4-carboxylateAusbeute 70,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

tert-Butyl 2-(4-acetylphenyl)morpholine-4-carboxylate (210 mg, 0.69 mmol) was dissolved in THF (3.5 ml). Lithium-bis-(trimethylsilyl)-amide solution (2.05 ml, 2.05 mmol, 1.0 M solution in THF) was added dropwise and the yellow reaction mixture was stirred at −78° C. for 1 hour. 4-Chlorobenzoyl chloride (120 mg, 0.69 mmol) was added and the reaction mixture was stirred for 90 min and was quenched by addition of 1M aqueous hydrochloric acid. Ethyl acetate was added and the organic layer was dried over MgSO4 and evaporated. The crude material was purified by flash chromatography (10 g silica gel, 10 to 50% ethyl acetate in heptane) to yield an off-white solid (215 mg, 70%). MS (ISP): 388.2 ([{35Cl}M-tBu+H]+), 390.3 ([{37Cl}M-tBu+H]+).

Aufarbeitung

  1. stirringthe reaction mixture was stirred for 90 min
  2. customwas quenched by addition of 1M aqueous hydrochloric acid
  3. additionEthyl acetate was added
  4. dry with materialthe organic layer was dried over MgSO4
  5. customevaporated
  6. customThe crude material was purified by flash chromatography (10 g silica gel, 10 to 50% ethyl acetate in heptane)

Quellen und Nachweise

ORD-Eintrag
ord-ae9c480ffaaa497b92be4b038445ee85
Quelldatensatz
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09181230B2

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