Ammonium Chloride → HCID 66587953, 화합물

HRID 530926

반응식

HRID 530926 반응식
[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

참가 물질

8

반응물 4

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

생성물 1

HCID 66587953HCID 66587953, 화합물수율 48.9%

시약·촉매·용매 3

HCID 962Water용매HCID 8028Tetrahydrofuran용매HCID 21226206Ethyl acetate hexane용매

반응 조건

온도
-65 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-8a9d3c6b9d004ceab18b43b791ed9aa9
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09353113B2

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