Ethanethiol → HCID 59948695、化合物

HRID 1532876ノート

反応式

HRID 1532876 の反応式
[CH2:1]([SH:3])[CH3:2].[H-].[Na+].[CH:6]1([CH2:12][C@H:13]2[CH2:15][O:14]2)[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1.[NH4+].[Cl-]>CN(C=O)C>[CH:6]1([CH2:12][C@H:13]([OH:14])[CH2:15][S:3][CH2:1][CH3:2])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1

参加物

6

反応物 4

HCID 6343EthanethiolHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 59949024HCID 59949024、化合物

生成物 1

HCID 59948695HCID 59948695、化合物収率 81.7%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

Ethanethiol (317 μL, 4.3 mmol) was added to a 60% dispersion in mineral oil NaH (180 mg, 4.5 mmol) slurry in DMF (26 mL) at ambient temperature. After stirring for 15 min, the product from Example 1308C (300 mg, 2.1 mmol) in DMF (2.0 mL) was added to the reaction vessel. After stirring for 30 min, a solution of saturated NH4Cl was added to the mixture followed by extraction with EtOAc (2×). The organics were combined, dried (MgSO4) and concentrated. The residue was chromatographed (silica gel; EtOAc/hexanes 1:20) to afford a light yellow oil (347 mg, 80%). 1H NMR (CDCl3, 300 MHz) δ0.80-1.00 (m, 2H), 1.12-1.32 (m, 7H), 1.39-1.75 (m, 6H), 1.81 (m, 1H), 2.42 (dd, J=9, 14 Hz, 1H), 2.56 (q, J=7.5 Hz, 2H), 2.74 (dd, J=3, 14 Hz, 1H), 3.76 (m, 1H); MS (CI/NH3) m/z: 203 (M+H)+.

後処理

  1. stirringAfter stirring for 30 min
  2. extractionfollowed by extraction with EtOAc (2×)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe residue was chromatographed (silica gel; EtOAc/hexanes 1:20)

出典と根拠

ORDレコード
ord-9a5010c207964655a3c43f1797929f7e
出典データセット
uspto-grants-2001_03
特許番号
US06204293B1

反応ノート

読み込み中…