Dichloromethane → HCID 10877890, 화합물

HRID 1523001노트

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HRID 1523001 반응식
[C:1]([OH:6])#[C:2][CH2:3][CH2:4][CH3:5].C(Cl)Cl.[C:10](Cl)([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:11]>CN(C1C=CN=CC=1)C.CCN(CC)CC>[C:10]([O:6][CH2:1][CH2:2][CH2:3][C:4]#[CH:5])(=[O:11])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

참가 물질

6

반응물 3

HCID 6344DichloromethaneHCID 7412Benzoyl chlorideHCID 10866258Pentynol

생성물 1

HCID 10877890HCID 10877890, 화합물수율 89.2%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 8471Triethylamine용매

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온도
0 °C

실험 절차

To a flame-dried round-bottomed flask was added pentynol (1 equiv., 24 mmol, 2.0 g) and CH2Cl2 (80 mL). The solution was cooled to 0° C. and BzCl (1.2 equiv., 28 mmol, 3.3 mL) was added dropwise, followed by DMAP (0.1 equiv., 2.4 mmol, 300 mg), and Et3N (7 mL). The reaction was warmed to ambient temperature over 12 h, quenched with 2N HCl (10 mL), extracted with EtOAc (2×40 mL), washed with brine (40 mL) and dried over Na2SO4. The purified product was isolated by concentrating in vacuo and purifying by flash chromatography (2.5% EtOAc/Hex) to afford pent-4-yn-1-yl benzoate (4.02 g, 21.4 mmol, 89%). TLC Rf=0.57 (10% EtOAc/Hex); 1HNMR (600 MHz): δ 8.03-8.07 (2H), 7.53-7.60 (1H), 7.42-7.48 (2H), 4.44 (t, 2H, J=6.1 Hz), 2.40 (td, 2H, J=7.3, 2.7 Hz), 1.98-2.05 (overlapping signals, 3H); 13CNMR (150 MHz): δ166.5, 132.9, 130.3, 129.6, 128.3, 83.0, 69.1, 63.4, 27.7, 15.4.

후처리

  1. temperatureThe reaction was warmed to ambient temperature over 12 h
  2. customquenched with 2N HCl (10 mL)
  3. extractionextracted with EtOAc (2×40 mL)
  4. washwashed with brine (40 mL)
  5. dry with materialdried over Na2SO4
  6. customThe purified product was isolated
  7. concentrationby concentrating in vacuo
  8. custompurifying by flash chromatography (2.5% EtOAc/Hex)

출처 및 근거

ORD 기록
ord-6acc0efc76f9467fba54a7ed2f884773
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09079835B2

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