Pyrrolidine → 6-Bromo-3-methyl-2',4',5',6'-tetrahydrospiro[chroman-2,3'-pyran]-4-one

HRID 1408730

반응식

HRID 1408730 반응식
[Br:1][C:2]1[CH:3]=[CH:4][C:5](O)=[C:6]([C:8](=[O:11])[CH2:9][CH3:10])[CH:7]=1.[O:13]1[CH2:18][CH2:17][CH2:16][C:15](=[O:19])[CH2:14]1.N1CCCC1>CO>[Br:1][C:2]1[CH:7]=[C:6]2[C:5](=[CH:4][CH:3]=1)[O:19][C:15]1([CH2:16][CH2:17][CH2:18][O:13][CH2:14]1)[CH:9]([CH3:10])[C:8]2=[O:11]

참가 물질

5

반응물 3

HCID 31268PyrrolidineHCID 901092H-Pyran-3(4H)-one, dihydro-HCID 7364091-(5-Bromo-2-hydroxyphenyl)propan-1-one

생성물 1

HCID 584240286-Bromo-3-methyl-2',4',5',6'-tetrahydrospiro[chroman-2,3'-pyran]-4-one수율 16%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

A mixture of 1-(5-bromo-2-hydroxyphenyl)propan-1-one (5.7 g, 25 mol), dihydro-2H-pyran-3(4H)-one (5 g, 50 mmol) and pyrrolidine (3.4 g, 48 mmol) in methanol (80 mL) was stirred overnight. The reaction mixture was removed in vacuo, and H2O was added. The resulting solution was extracted with ethyl acetate. The ethyl acetate solution was dried over anhydrous Na2SO4, filtered, and evaporated to give 6-bromo-3-methyl-2′,4′,5′,6′-tetrahydrospiro[chroman-2,3′-pyran]-4-one (1.2 g, 16%). 1HNMR (CDCl3): 1.16-1.27 (m, 3H), 1.51-1.57 (m, 1H), 1.66-1.73 (m, 1H), 1.91-2.08 (m, 2H), 2.59-2.69 (m, 1H), 3.46-3.56 (m, 2H), 3.88-3.98 (m, 2H), 6.97 (m, 1H), 7.58 (m, 1H), 7.95 (s, 1H).

후처리

  1. customThe reaction mixture was removed in vacuo, and H2O
  2. additionwas added
  3. extractionThe resulting solution was extracted with ethyl acetate
  4. dry with materialThe ethyl acetate solution was dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. customevaporated

출처 및 근거

ORD 기록
ord-d0e3ba3219f940008f149451505247c9
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08921359B2

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