Triphenylphosphine → HCID 14534130, 화합물

HRID 9816노트

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HRID 9816 반응식
[CH2:1](O)[CH2:2][C:3]#[C:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1C(=O)N([Br:38])C(=O)C1>CN(C=O)C>[Br:38][CH2:1][CH2:2][C:3]#[C:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

참가 물질

5

반응물 3

HCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 1039403-Decyn-1-ol

생성물 1

HCID 14534130HCID 14534130, 화합물수율 72.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
0 °C

실험 절차

To a solution of dec-3-yn-1-ol (1.54 g, 10.0 mmol) in DMF (25 mL) was added triphenylphosphine (2.92 g, 11.2 mmol). The solution was cooled to 0° C. and NBS (1.92 g, 10.8 mmol) was added in portions. After stirring for 30 min at room temperature, the reaction was quenched with methanol (1 mL). The solution was diluted with ether (150 mL), washed with water, saturated aqueous NaHCO3 and brine successively. The organic layer was dried and concentrated. The residue was purified by flash chromatography on silica gel, eluting with hexane to afford 1-bromo-dec-3-yne (1.57 g, 72%) as a colorless oil: 1H NMR (300 MHz, CDCl3) δ 3.40 (2H, d, J=7.2 Hz), 2.70 (2H, m), 2.14 (2H, m), 1.20–1.55 (8H, m), 0.88 (3H, t, J=6.9 Hz); 13C NMR (75 MHz, CDCl3) δ 82.89, 77.05, 31.62, 30.68, 29.06, 28.78, 23.65, 22.86, 18.99, 13.38.

후처리

  1. customthe reaction was quenched with methanol (1 mL)
  2. additionThe solution was diluted with ether (150 mL)
  3. washwashed with water, saturated aqueous NaHCO3 and brine successively
  4. customThe organic layer was dried
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography on silica gel
  7. washeluting with hexane

출처 및 근거

ORD 기록
ord-3f6ffb5c828b48f4b62716112b437464
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091357B2

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