HCID 58762434、化合物 → HCID 58762453、化合物

HRID 1453008ノート

反応式

HRID 1453008 の反応式
[CH:1]1([Mg]Br)[CH2:5][CH2:4][CH2:3][CH2:2]1.N1C=CC=CC=1S[C:15](=[O:24])[CH2:16][CH2:17][C:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH:19]=1>CCOCC.C1COCC1>[C:18]1([CH2:17][CH2:16][C:15]([CH:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)=[O:24])[CH2:23][CH2:22][CH2:21][CH2:20][CH:19]=1

参加物

5

反応物 2

HCID 58762434HCID 58762434、化合物HCID 178419650HCID 178419650、化合物

生成物 1

HCID 58762453HCID 58762453、化合物収率 72%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

Cyclopentylmagnesium bromide (1.6 mL, 3.15 mmol, 2M soln in ether) was added to a cooled −78° C. solution of 3-Cyclohex-1-enyl-thiopropionic acid S-pyridin-2-yl ester (0.65 g, 2.63 mmol, from Step 3) dissolved in THF (10 mL). The reaction mixture was stirred for 45 min at −78° C. and then warmed up to rt. The reaction was quenched with 1N HCl and extracted with EtOAc. The organic layer was washed with saturated NaHCO3, brine, dried over Na2SO4 and concentrated. The residue was purified by silica gel chromatography (0% to 5% EtOAc in hexanes) to give the title compound as a clear oil (0.39 g, 72%). 1H NMR (CDCl3): δ 1.51-1.83 (br m, 12H), 1.91 (m, 2H), 1.97 (m, 2H), 2.20 (t, 2H, J=7.6 Hz), 2.54 (t, 2H, J=7.8 Hz), 2.87 (m, 1H), 5.39 (s, 1H).

後処理

  1. temperaturewarmed up to rt
  2. customThe reaction was quenched with 1N HCl
  3. extractionextracted with EtOAc
  4. washThe organic layer was washed with saturated NaHCO3, brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography (0% to 5% EtOAc in hexanes)

出典と根拠

ORDレコード
ord-2872d36e85d140009ee7c5b5a2d711bd
出典データセット
uspto-grants-2009_01
特許番号
US07473790B2

反応ノート

読み込み中…