Ethyl Acetate → rac-3,4-Dihydro-2,5,7,8-tetramethyl-2-[(3-pyridinyl)ethynyl]-2H-1-benzopyran-6-ol

HRID 256836

反応式

HRID 256836 の反応式
[C:1]([C:3]1([CH3:17])[CH2:8][CH2:7][C:6]2[C:9]([CH3:16])=[C:10]([OH:15])[C:11]([CH3:14])=[C:12]([CH3:13])[C:5]=2[O:4]1)#[CH:2].Br[C:19]1[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=1.C(OCC)(=O)C>C(Cl)Cl>[CH3:17][C:3]1([C:1]#[C:2][C:19]2[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=2)[CH2:8][CH2:7][C:6]2[C:9]([CH3:16])=[C:10]([OH:15])[C:11]([CH3:14])=[C:12]([CH3:13])[C:5]=2[O:4]1

参加物

5

反応物 3

HCID 8857Ethyl AcetateHCID 122863-BromopyridineHCID 14478563rac-3,4-dihydro-2-ethynyl-2,5,7,8-tetramethyl-2H-1-benzopyran-6ol

生成物 1

HCID 15171813rac-3,4-Dihydro-2,5,7,8-tetramethyl-2-[(3-pyridinyl)ethynyl]-2H-1-benzopyran-6-ol

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Rac-3,4-dihydro-2-ethynyl-2,5,7,8-tetramethyl-2H-1-benzopyran-6-ol, 4.6 g, was reacted as described in Example 4 with 4.74 g of 3-bromopyridine. The reaction time was extended to 18 hours. The product was isolated by chromatography over 150 g of silica gel using 10% (v/v) of ethyl acetate in methylene chloride for elution. Crystallization of the combined clean fractions from ethyl acetate/hexane gave off-white crystals with m.p. 172°-175° C. The analytical sample was recrystallized from tetrahydrofuran/hexane and had m.p. 175°-178° C.

後処理

  1. customCrystallization of the combined clean fractions from ethyl acetate/hexane
  2. customgave off-white crystals with m.p. 172°-175° C
  3. customThe analytical sample was recrystallized from tetrahydrofuran/hexane

出典と根拠

ORDレコード
ord-ef63629a95bb4a5d9d16afb8510bb459
出典データセット
uspto-grants-1993_11
特許番号
US05260294

関連ノート

読み込み中…