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Diisopropylethylamine → HCID 23655183, 화합물

HRID 2059528
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HRID 2059528 반응식
[C:1]([O:5][C:6]([NH:8][C:9]1(/[CH:17]=[CH:18]/[C:19]2[CH:24]=[CH:23][C:22](Br)=[CH:21][CH:20]=2)[CH2:14][O:13][C:12]([CH3:16])([CH3:15])[O:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:26]([O:33][CH2:34][CH2:35][CH2:36][C:37]#[CH:38])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C(N(CC)C(C)C)(C)C>C1COCC1.[Cu]I.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]([O:5][C:6]([NH:8][C:9]1(/[CH:17]=[CH:18]/[C:19]2[CH:24]=[CH:23][C:22]([C:38]#[C:37][CH2:36][CH2:35][CH2:34][O:33][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[CH:21][CH:20]=2)[CH2:14][O:13][C:12]([CH3:16])([CH3:15])[O:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 3

HCID 81531DiisopropylethylamineHCID 563055((Pent-4-yn-1-yloxy)methyl)benzeneHCID 23655027HCID 23655027, 화합물

생성물 1

HCID 23655183HCID 23655183, 화합물수율 54.3%

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매
HCID 178418397
HCID 178418397, 화합물
촉매
HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 17 (0.21 g, 0.51 mmol) and 5-benzyloxy-1-pentyne (133 mg, 0.77 mmol) in N,N-diisopropylethylamine (1 mL, 5.7 mmol) and dry THF (5 mL) were added CuI (9.7 mg, 51 μmol) and tetrakis(triphenylphosphine)palladium(0) (29.5 mg, 25.5 μmol) under nitrogen. The mixture was heated at reflux under nitrogen for one day, and then was cooled to room temperature and filtered through a short pad of silica gel to remove insoluble and very polar components in the mixture. The filtrate was concentrated and dissolved in CH2Cl2 (50 mL). The solution was washed with water (2×20 mL) and brine (2×20 mL), and dried over Na2SO4. The solvent was removed under vacuum and the residue was purified by column chromatography (hexanes/EtOAc 20:1 to 6:1) to give 18 (0.14 g, 53%). 1H NMR δ 7.43-7.19 (m, 4H), 6.49 (d, 1H, J=16.4 Hz), 6.21 (d, 1H, J=16.4 Hz), 5.43 (s, 1H), 4.50 (s, 2H), 3.98 (d, 2H, J=11.2 Hz), 3.87 (d, 2H, J=11.2 Hz), 3.59 (t, 2H, J=6.0 Hz), 2.53 (t, 2H, J=6.8 Hz), 1.89 (m, 2H), 1.45 (s, 15H); 13C NMR δ 154.4, 138.1, 135.5, 131.3, 129.3, 127.9, 127.2, 127.1, 125.9, 122.8, 97.8, 90.1, 80.6, 79.0, 72.5, 68.3, 65.6, 52.7, 28.5, 28.0, 27.1, 19.3, 15.9. HRMS m/z: calcd for C31H39NNaO5 (MNa+), 528.2720; found, 528.2727.

후처리

  1. temperatureThe mixture was heated
  2. temperatureat reflux under nitrogen for one day
  3. filtrationfiltered through a short pad of silica gel
  4. customto remove insoluble
  5. concentrationThe filtrate was concentrated
  6. dissolutiondissolved in CH2Cl2 (50 mL)
  7. washThe solution was washed with water (2×20 mL) and brine (2×20 mL)
  8. dry with materialdried over Na2SO4
  9. customThe solvent was removed under vacuum
  10. customthe residue was purified by column chromatography (hexanes/EtOAc 20:1 to 6:1)

출처 및 근거

ORD 기록
ord-72fa96aca7a4430db9091c1fcce385a5
출처 데이터셋
uspto-grants-2012_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08277775B2

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