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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
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HRID 2099753 반응식
[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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 10774245alpha-CyclohexylcyclohexanemethanamineHCID 69071650ethyl 4-(7-methyl-1H-indazol-5-yl)but-2-enoate

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran
용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-e71646ec3a1b4e5f8010413664429879
출처 데이터셋
uspto-grants-2009_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07569578B2

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