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2-(Trimethylsilyl)ethanethiol → 3-Cyano-1-(furan-3-yl)-6-[2-trimethylsilylethylthio]naphthalene

HRID 741835
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HRID 741835 반응식
[C:1]([C:3]1[CH:4]=[C:5]([C:14]2[CH:18]=[CH:17][O:16][CH:15]=2)[C:6]2[C:11]([CH:12]=1)=[CH:10][C:9](I)=[CH:8][CH:7]=2)#[N:2].[CH3:19][Si:20]([CH3:25])([CH3:24])[CH2:21][CH2:22][SH:23].CC(C)([O-])C.[K+]>CCO.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:1]([C:3]1[CH:4]=[C:5]([C:14]2[CH:18]=[CH:17][O:16][CH:15]=2)[C:6]2[C:11]([CH:12]=1)=[CH:10][C:9]([S:23][CH2:22][CH2:21][Si:20]([CH3:25])([CH3:24])[CH3:19])=[CH:8][CH:7]=2)#[N:2]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 2055212-(Trimethylsilyl)ethanethiolHCID 233702222-Cyano-4-(3-furyl)-7-iodonaphthaleneHCID 23665647Potassium tert-butoxide

생성물 1

HCID 194269713-Cyano-1-(furan-3-yl)-6-[2-trimethylsilylethylthio]naphthalene수율 70.6%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매
HCID 702Ethanol용매

실험 절차

A mixture of 3-cyano-1-(furan-3-yl)-6-iodonaphthalene (2.5 g, 7.25 mmol), 2-(trimethylsilyl)ethanethiol (974 mg, 7.25 mmol), potassium tert-butoxide (1.624 g, 14.5 mmol) and (Ph3P)4Pd (200 mg, 0.17 mmol) in EtOH (250 mL) was refluxed for 6.5 h. After evaporation of the EtOH, the residue was partitioned between Et2O and H2O. The crude product from the organic phase was chromatographed on silica gel, eluting with a 1:9 mixture of EtOAc and hexane to afford the title product (1.8 g) as an amber oil.

후처리

  1. temperaturewas refluxed for 6.5 h
  2. customAfter evaporation of the EtOH
  3. customthe residue was partitioned between Et2O and H2O
  4. customThe crude product from the organic phase was chromatographed on silica gel
  5. washeluting with a 1:9 mixture of EtOAc and hexane

출처 및 근거

ORD 기록
ord-12bc4385c80a4ea0989c0e8be00cd388
출처 데이터셋
uspto-grants-1996_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05552437

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