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2-Hexynoic Acid → HCID 18008055, 화합물

HRID 988245
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HRID 988245 반응식
I[C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][CH:19]=1)[O:5][CH2:6][C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=1.[C:20]([OH:27])(=[O:26])[C:21]#[C:22][CH2:23][CH2:24][CH3:25]>N1CCCCC1.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>[CH:8]1[C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:15]=[CH:16][C:7]=1[CH2:6][O:5][C:4]1[CH:3]=[C:2]([C:25]#[C:24][CH2:23][CH2:22][CH2:21][C:20]([OH:27])=[O:26])[CH:19]=[CH:18][CH:17]=1
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참가 물질

5

반응물 2

HCID 3243802-Hexynoic AcidHCID 18008068HCID 18008068, 화합물

생성물 1

HCID 18008055HCID 18008055, 화합물

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매HCID 8082Piperidine용매

반응 조건

온도
75 °C

실험 절차

A solution of 2-(3-iodophenoxymethyl)-naphthalene (0.5 g, 1.4 mmol) and hexynoic acid (0.19 g, 1.7 mmol) in piperidine (5 mL) is purged with Argon for 20 minutes. Then bis(triphenylphosphine)palladium dichloride (0.01 g, 0.014 mmol) and cuprous iodide (0.005 g, 0.028 mmol) are added and this mixture heated in an oil bath at 75° C. for 1.5 hours and then allowed to come to room temperature overnight. The solvent was removed in vacuo and the residue purified by flash chromatography (silica, 4% methanol in dichloromethane) to give the title compound. 1H NMR (300 MHz, CDCl3) δ 7.83-7.88 (m, 4H), 7.48-7.54 (m, 3H), 7.19 (t, 1H), 6.98-7.05 (m, 3H), 5.21 (s, 2H), 2.47 (t, 2H), 1.80-1.91 (m, 4H); MS (EI) 344 (M)+.

후처리

  1. customThe solvent was removed in vacuo
  2. customthe residue purified by flash chromatography (silica, 4% methanol in dichloromethane)

출처 및 근거

ORD 기록
ord-526e984603984e6a97d5102c1e69a371
출처 데이터셋
uspto-grants-2003_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06635655B1

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