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

HRID 256836

반응식

HRID 256836 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-ef63629a95bb4a5d9d16afb8510bb459
출처 데이터셋
uspto-grants-1993_11
특허 번호
US05260294

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