Allyl bromide → Cyclopropanecarboxylic acid, 1-(2-propenyl)-, 1,1-dimethylethyl ester

HRID 501346

反応式

HRID 501346 の反応式
C([N-][CH:5]([CH3:7])[CH3:6])(C)C.[Li+].C(NC(C)C)(C)C.C([Li])CCC.[C:21]([O:25][C:26]([CH:28]1[CH2:30][CH2:29]1)=[O:27])([CH3:24])([CH3:23])[CH3:22].C(Br)C=C.[Cl-].[NH4+]>C1COCC1>[C:21]([O:25][C:26]([C:28]1([CH2:7][CH:5]=[CH2:6])[CH2:30][CH2:29]1)=[O:27])([CH3:24])([CH3:23])[CH3:22]

参加物

8

反応物 6

HCID 7841Allyl bromideHCID 7912DiisopropylamineHCID 25517Ammonium ChlorideHCID 2724682Lithium diisopropylamideHCID 13676038tert-Butyl cyclopropanecarboxylateHCID 178418339Butyllithium

生成物 1

HCID 546367Cyclopropanecarboxylic acid, 1-(2-propenyl)-, 1,1-dimethylethyl ester

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

反応条件

温度
0 °C

実験手順

Lithium diisopropyl amide was generated from 7.5 g (58.1 mmol) diisopropyl amine and 23.2 mL of 2.5 M n-butyl lithium in 200 mL THF at 0° C. under nitrogen. After stirring for 30 minutes at 0° C. the solution was taken to −78° C. where 7.5 g (52.8 mmol) of cyclopropanecarboxylic acid tert-butyl ester in 30 mL of THF was added dropwise over 5 min. After 4 h 12.8 g (106 mmol) of allyl bromide in 30 mL THF was added drop-wise over 10 min. to the clear golden solution. The reaction was allowed to slowly warm to room temperature. After 19 hours the reaction was poured into aqueous saturated ammonium chloride solution, extracted with ether, dried and concentrated to deliver an oil which was purified via Kugelrohr distillation (approx. 20 mm Hg; 60-75° C. oven) to deliver 5.4 g (56%) of the desired product as a clear colorless oil.

後処理

  1. customwas taken to −78° C.
  2. additionwas added dropwise over 5 min
  3. temperatureto slowly warm to room temperature
  4. extractionextracted with ether
  5. customdried
  6. concentrationconcentrated
  7. distillationwas purified via Kugelrohr distillation (approx. 20 mm Hg; 60-75° C. oven)

出典と根拠

ORDレコード
ord-cd50aaf9d15340dab3af8fe37511a97a
出典データセット
uspto-grants-2010_08
特許番号
US07772252B2

関連ノート

読み込み中…