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

HRID 710237
ノート
印刷プレビュー

反応式

HRID 710237 の反応式
[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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

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

生成物 1

HCID 89689396tert-Butyl 2-(4-(3-(4-chlorophenyl)-3-oxopropanoyl)phenyl)morpholine-4-carboxylate収率 70.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

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]+).

後処理

  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)

出典と根拠

ORDレコード
ord-ae9c480ffaaa497b92be4b038445ee85
出典データセット
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09181230B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート