Ammonium Chloride → HCID 66587953、化合物

HRID 530926

反応式

HRID 530926 の反応式
[CH:1]1([C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5])[CH2:3][CH2:2]1.Br[CH2:12][CH2:13][CH2:14][CH2:15][O:16][CH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][O:18]1.C([N-]C(C)C)(C)C.[Li+].[Cl-].[NH4+]>CCCCCC.C(OCC)(=O)C.O.C1COCC1>[O:18]1[CH2:19][CH2:20][CH2:21][CH2:22][CH:17]1[O:16][CH2:15][CH2:14][CH2:13][CH2:12][C:1]1([C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5])[CH2:3][CH2:2]1

参加物

8

反応物 4

HCID 25517Ammonium ChlorideHCID 5590192-(4-Bromobutoxy)tetrahydro-2H-pyranHCID 2724682Lithium diisopropylamideHCID 13676038tert-Butyl cyclopropanecarboxylate

生成物 1

HCID 66587953HCID 66587953、化合物収率 48.9%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒HCID 21226206Ethyl acetate hexane溶媒

反応条件

温度
-65 °C

実験手順

Under the argon atmosphere, tert-butyl cyclopropylcarboxylate (3.76 g) and 2-(4-bromobutoxy)tetrahydro-2H-pyran (7.52 g) were dissolved in anhydrous/THF (106 mL), followed by cooling to an inner temperature of −65° C. A lithium diisopropylamide solution (2.0M, THF:heptane:ethylbenzene solution) (19.8 mL) was added dropwise over 15 minutes. After completion of addition, the mixture was stirred at room temperature for 8 hours. An aqueous saturated ammonium chloride solution was added to stop the reaction, and water, and hexane:ethyl acetate (1:1) were added, followed by extraction. The organic layer was washed with dilute hydrochloric acid, water and an aqueous saturated sodium chloride solution, and dried with anhydrous sodium sulfate. The residue obtained by concentration was purified by silica gel column chromatography (hexane:ethyl acetate, 98:2→90:10) to obtain the title compound (3.86 g) having the following physical property values.

後処理

  1. additionAfter completion of addition
  2. additionwere added
  3. extractionfollowed by extraction
  4. washThe organic layer was washed with dilute hydrochloric acid, water
  5. dry with materialan aqueous saturated sodium chloride solution, and dried with anhydrous sodium sulfate
  6. customThe residue obtained by concentration
  7. customwas purified by silica gel column chromatography (hexane:ethyl acetate, 98:2→90:10)

出典と根拠

ORDレコード
ord-8a9d3c6b9d004ceab18b43b791ed9aa9
出典データセット
uspto-grants-2016_05
特許番号
US09353113B2

関連ノート

読み込み中…