Propylene Oxide → 1-[2-(2-Dimethylamino-ethyl)-benzo[b]thiophen-3-yl]-propan-2-ol

HRID 746629ノート

反応式

HRID 746629 の反応式
Br[C:2]1[C:3]2[CH:15]=[CH:14][CH:13]=[CH:12][C:4]=2[S:5][C:6]=1[CH2:7][CH2:8][N:9]([CH3:11])[CH3:10].CN(CCN(C)C)C.[Li]CCCC.[CH3:29][CH:30]1[CH2:32][O:31]1>C1(C)C=CC=CC=1>[CH3:10][N:9]([CH3:11])[CH2:8][CH2:7][C:6]1[S:5][C:4]2[CH:12]=[CH:13][CH:14]=[CH:15][C:3]=2[C:2]=1[CH2:29][CH:30]([OH:31])[CH3:32]

参加物

6

反応物 4

HCID 6378Propylene OxideHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 58591562[2-(3-Bromo-benzo[b]thiophen-2-yl)-ethyl]-dimethyl-amineHCID 178418339Butyllithium

生成物 1

HCID 585915821-[2-(2-Dimethylamino-ethyl)-benzo[b]thiophen-3-yl]-propan-2-ol収率 17.5%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
-78 °C

実験手順

A solution of [2-(3-bromo-benzo[b]thiophen-2-yl)-ethyl]-dimethyl-amine (285 mg, 1 mmol) and TMEDA (181 uL, 1.2 mmol) in toluene (12 mL) was cooled to −78° C. n-BuLi (750 uL, 1.2 mmol, 1.6M in hexanes) was added and the reaction was stirred at −78° C. for 45 min. 2-Methyl-oxirane (280 uL, 4 mmol) was added at −78° C. and the reaction was allowed to slowly reach room temperature, while being stirred overnight. The reaction was quenched with NH4Cl, pH was adjusted with sat. NaHCO3 until pH ˜9, followed by an extraction with EtOAc (4×). The combined organic layers were washed with brine, dried (MgSO4) and concentrated. Silica gel column chromatography (eluent: dichloromethane with gradient up to dichloromethane/MeOH=97/3) afforded 46 mg of 1-[2-(2-dimethylamino-ethyl)-benzo[b]thiophen-3-yl]-propan-2-ol (Compound 23-1).

後処理

  1. additionwas added
  2. customwas allowed to slowly reach room temperature
  3. stirringwhile being stirred overnight
  4. customThe reaction was quenched with NH4Cl, pH
  5. extractionfollowed by an extraction with EtOAc (4×)
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-bfae3bb45baf43808f2e7529f7f9209f
出典データセット
uspto-grants-2008_07
特許番号
US07393865B2

反応ノート

読み込み中…