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

HRID 1408730

反応式

HRID 1408730 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-d0e3ba3219f940008f149451505247c9
出典データセット
uspto-grants-2014_12
特許番号
US08921359B2

関連ノート

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