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Ethyl 4-iodobenzoate → Ethyl4-[4-(1-benzyloxycyclopropyl)-phenylethynyl]-benzoate

HRID 278717
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HRID 278717 반응식
[CH:1]([O:4][C:5]1([C:8]2[CH:13]=[CH:12][C:11]([C:14]#[C:15][C:16]3[CH:26]=[CH:25][C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:18][CH:17]=3)=[CH:10][CH:9]=2)[CH2:7][CH2:6]1)([CH3:3])C.C(OC(=O)[C:31]1[CH:36]=[CH:35]C(I)=[CH:33][CH:32]=1)C>C(N(CC)CC)C.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:1]([O:4][C:5]1([C:8]2[CH:9]=[CH:10][C:11]([C:14]#[C:15][C:16]3[CH:26]=[CH:25][C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:18][CH:17]=3)=[CH:12][CH:13]=2)[CH2:7][CH2:6]1)[C:3]1[CH:35]=[CH:36][CH:31]=[CH:32][CH:33]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 2

HCID 142891Ethyl 4-iodobenzoate2회HCID 22568976Ethyl4-[4-(1-isopropoxycyclopropyl)-phenylethynyl]-benzoate2회

생성물 1

HCID 22568905Ethyl4-[4-(1-benzyloxycyclopropyl)-phenylethynyl]-benzoate수율 91%

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매
HCID 178418476
HCID 178418476, 화합물
촉매
HCID 8471Triethylamine용매

실험 절차

Using General Procedure F; 1-ethynyl-4-(1-benzyloxycyclopropyl)-benzene (Intermediate 71, 60.0 mg, 0.24 mmol) and ethyl-4-iodo benzoate (Reagent A, 72.0 mg, 0.26 mmol) in triethylamine (4 mL) was treated with copper(I)iodide (17.0 mg, 0.09 mmol) and sparged with argon for 5 minutes. Dichlorobis(triphenylphosphine)palladium(II) (61 mg, 0.09 mmol) was added and the reaction mixture was stirred overnight at room temperature. Column chromatography (2-4% EtOAc-hexanes) afforded 85.0 mg (91%) of the title compound as an orange oil.

후처리

  1. customsparged with argon for 5 minutes

출처 및 근거

ORD 기록
ord-751c7883459f49178bc47c92c9aaa49d
출처 데이터셋
uspto-grants-2002_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06359135B1

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