3-Dipropylamino-5-chloroformyichroman → 3-Dipropylamino-5-acetylchroman

HRID 37649노트

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HRID 37649 반응식
[CH2:1]([N:4]([CH2:18][CH2:19][CH3:20])[CH:5]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][C:12]=2[C:15](Cl)=[O:16])[O:7][CH2:6]1)[CH2:2][CH3:3].[CH2:21](N(CCC)C1CC2C(=CC=CC=2C(OC)=O)OC1)CC.[Li]C>O1CCCC1.[Cu]I>[CH2:1]([N:4]([CH2:18][CH2:19][CH3:20])[CH:5]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][C:12]=2[C:15](=[O:16])[CH3:21])[O:7][CH2:6]1)[CH2:2][CH3:3]

참가 물질

6

반응물 3

HCID 190280843-Dipropylamino-5-chloroformyichromanHCID 190280933-Dipropylamino-5-methyloxycarbonylchromanHCID 178418348HCID 178418348, 화합물

생성물 1

HCID 102212133-Dipropylamino-5-acetylchroman

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 8028Tetrahydrofuran용매2회

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온도
-78 °C

실험 절차

3-Dipropylamino-5-chloroformylchroman*HCl (4.42 g, 13.4 mmol), prepared from 3-dipropylamino-5-methyloxycarbonylchroman (Example 2) analogous to the procedure used in Example 3, in dry tetrahydrofuran (20 ml), was added to a pre-formed solution of lithium dimethylcuprate; prepared from MeLi and CuI, in 200 mL tetrahydrofuran at -78° C. The solution was stirred for 15 minutes at -78° C. and was then allowed to reach room temperature during 10 minutes. Then, 30 mL H20 was slowly added. The organic phase was decanted, dried with Na2SO4 and evaporated to dryness. The residue was purified by flash chromatography (silica gel) by elution with ethyl acetate/hexane 1:8. The title compound was crystallized as salt from ethyl acetate. Mp 106°-108° C. (oxalate).

후처리

  1. waitto reach room temperature during 10 minutes
  2. additionThen, 30 mL H20 was slowly added
  3. customThe organic phase was decanted
  4. dry with materialdried with Na2SO4
  5. customevaporated to dryness
  6. customThe residue was purified by flash chromatography (silica gel) by elution with ethyl acetate/hexane 1:8
  7. customThe title compound was crystallized as salt from ethyl acetate

출처 및 근거

ORD 기록
ord-be46729521be46dc9b9e591301f42c4d
출처 데이터셋
uspto-grants-1995_05
특허 번호
US05420151

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