Allyl bromide → N-(4-Acetyl-5-benzyloxy-2-bromo-phenyl)-N-allyl-acetamide

HRID 1433159ノート

反応式

HRID 1433159 の反応式
[C:1]([C:4]1[C:9]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:8][C:7]([NH:18][C:19](=[O:21])[CH3:20])=[C:6]([Br:22])[CH:5]=1)(=[O:3])[CH3:2].[Li+].[CH3:24][CH:25]([N-]C(C)C)[CH3:26].C(Br)C=C>C1COCC1>[C:1]([C:4]1[C:9]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:8][C:7]([N:18]([CH2:26][CH:25]=[CH2:24])[C:19](=[O:21])[CH3:20])=[C:6]([Br:22])[CH:5]=1)(=[O:3])[CH3:2]

参加物

5

反応物 3

HCID 7841Allyl bromideHCID 2724682Lithium diisopropylamideHCID 69059837N-(4-Acetyl-5-benzyloxy-2-bromo-phenyl)-acetamide

生成物 1

HCID 57934833N-(4-Acetyl-5-benzyloxy-2-bromo-phenyl)-N-allyl-acetamide収率 58%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

A solution of N-(4-acetyl-5-benzyloxy-2-bromo-phenyl)-acetamide (1.03 g, 2.85 mmol) in anhydrous THF (20 ml) under nitrogen was cooled to −78° C. followed by the dropwise addition of LDA (2.1 ml, 2M solution, 4.3 mmol). The reaction was continued to stir for an hour at −78° C. and then quenched with allyl bromide (0.44 ml, 2.85 mmol). The reaction was allowed to warm to room temperature and continued to stir overnight. The solution was partitioned between EtOAc and water. The organics were collected and washed with water, brine and then dried (MgSO4). Purification by column chromatography in hexane/EtOAc (1:1) afforded a white solid (0.662 g, 58%). LC/MS: RT=2.703 min. 402/404 (MH+).

後処理

  1. temperatureto warm to room temperature
  2. stirringto stir overnight
  3. customThe solution was partitioned between EtOAc and water
  4. customThe organics were collected
  5. washwashed with water, brine
  6. dry with materialdried (MgSO4)
  7. customPurification by column chromatography in hexane/EtOAc (1:1)

出典と根拠

ORDレコード
ord-ac00bf304c034c559a71874a3180be30
出典データセット
uspto-grants-2009_11
特許番号
US07612201B2

反応ノート

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