Heptane → HCID 17806677、化合物

HRID 1363307ノート

反応式

HRID 1363307 の反応式
[CH2:1]([N:8]1[CH:12]=[CH:11][CH:10]=[C:9]1[C:13](OC)=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].C([Al+]CC(C)C)C(C)C.CCCCCCC>C(Cl)Cl>[CH2:1]([N:8]1[CH:12]=[CH:11][CH:10]=[C:9]1[CH2:13][OH:14])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 8900HeptaneHCID 21225700DiisobutylaluminumhydrideHCID 21766231Methyl 1-benzyl-1H-pyrrole-2-carboxylate

生成物 1

HCID 17806677HCID 17806677、化合物収率 88.4%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of methyl 1-benzyl-1H-pyrrole-2-carboxylate (3.00 g, 13.9 mmol) in DCM (70 mL) at −78° C. was added a 1M solution of diisobutylaluminum hydride (DIBAL-H) in heptane (35.0 mL, 34.8 mmol). After 45 min the reaction was quenched with saturated aqueous solution of NH4Cl (20 mL) and Rochell's salt (100 g). The mixture was allowed to warm to rt and was stirred for 2.5 h. The reaction mixture was extracted with EtOAc (3×). The combined organic layers were washed with H2O, saturated aq NaCl, dried over MgSO4, filtered and concentrated in vacuo to give a pale yellow oil. The crude product was chromatographed over silica gel (0 to 20% EtOAc in heptane over 20 min) to give (1-benzyl-1H-pyrrol-2-yl)-methanol as a colorless oil (2.30 g, 88%). Rf=0.47 (1:1 heptane/EtOAc); 1H NMR (400 MHz, CDCl3) δ (ppm) 7.27-7.35 (m, 4H) 7.08-7.10 (m, 1H) 7.06-7.08 (m, 1H) 6.73 (dd, J=2.7, 1.8 Hz, 1H) 6.19 (dd, J=3.5, 1.8 Hz, 1H) 6.12-6.16 (m, 1H) 5.21-5.23 (s, 2H) 4.53 (d, J=5.1 Hz, 2H).

後処理

  1. customAfter 45 min the reaction was quenched with saturated aqueous solution of NH4Cl (20 mL) and Rochell's salt (100 g)
  2. extractionThe reaction mixture was extracted with EtOAc (3×)
  3. washThe combined organic layers were washed with H2O, saturated aq NaCl
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto give a pale yellow oil
  8. customThe crude product was chromatographed over silica gel (0 to 20% EtOAc in heptane over 20 min)

出典と根拠

ORDレコード
ord-04fe4e43fbee4af8802f30dc52b00577
出典データセット
uspto-grants-2011_02
特許番号
US07884124B2

反応ノート

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