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2-Chloromethyl 2-(trimethylsilyl)ethyl ether → Ethyl 4-(7-methyl-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-5-yl)but-2-enoate

HRID 2099753
ノート
印刷プレビュー

反応式

HRID 2099753 の反応式
[CH3:1][C:2]1[CH:3]=[C:4]([CH2:11][CH:12]=[CH:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:5]=[C:6]2[C:10]=1[NH:9][N:8]=[CH:7]2.C1(C(N)C2CCCCC2)CCCCC1.[CH3:33][Si:34]([CH3:41])([CH3:40])[CH2:35][CH2:36][O:37][CH2:38]Cl>O1CCCC1>[CH3:1][C:2]1[C:10]2[C:6](=[CH:7][N:8]([CH2:38][O:37][CH2:36][CH2:35][Si:34]([CH3:41])([CH3:40])[CH3:33])[N:9]=2)[CH:5]=[C:4]([CH2:11][CH:12]=[CH:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:3]=1
参加物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 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 10774245alpha-CyclohexylcyclohexanemethanamineHCID 69071650ethyl 4-(7-methyl-1H-indazol-5-yl)but-2-enoate

生成物 1

HCID 69069206Ethyl 4-(7-methyl-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-5-yl)but-2-enoate収率 93%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran
溶媒

実験手順

To the clear solution of ethyl 4-(7-methyl-1H-indazol-5-yl)but-2-enoate (760 mg, 3.11 mmol, 1.0 equiv.) in tetrahydrofuran (10 mL) was added dicyclohexylmethyl amine (2.6 mL, 6.2 mL, 2.0 equiv) followed by 2-(trimethylsilyl)ethoxymethyl chloride (0.66 mL, 3.73 mmol, 1.2 equiv). The reaction mixture was stirred at room temperature for 2 h. The mixture was partitioned between 0.5 N sodium hydroxide and ethyl acetate. The organic layer was separated and washed with brine, dried over sodium sulfate and concentrated in vacuo. The residual colorless oil was purified by flash column chromatography (20% ethyl acetate in hexanes) to afford the desired product as a colorless oil (1.08 g, 93%). MS (ESI) [M+H]+=375.

後処理

  1. customThe mixture was partitioned between 0.5 N sodium hydroxide and ethyl acetate
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residual colorless oil was purified by flash column chromatography (20% ethyl acetate in hexanes)

出典と根拠

ORDレコード
ord-e71646ec3a1b4e5f8010413664429879
出典データセット
uspto-grants-2009_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07569578B2

反応ノート

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