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

HRID 1433159노트

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HRID 1433159 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
-78 °C

실험 절차

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+).

후처리

  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)

출처 및 근거

ORD 기록
ord-ac00bf304c034c559a71874a3180be30
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07612201B2

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