Dichloromethane → HCID 10877890、化合物

HRID 1523001ノート

反応式

HRID 1523001 の反応式
[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

参加物

6

反応物 3

HCID 6344DichloromethaneHCID 7412Benzoyl chlorideHCID 10866258Pentynol

生成物 1

HCID 10877890HCID 10877890、化合物収率 89.2%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 8471Triethylamine溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-6acc0efc76f9467fba54a7ed2f884773
出典データセット
uspto-grants-2015_07
特許番号
US09079835B2

反応ノート

読み込み中…