Bromobenzene → 2,2-Dimethyl-4-phenyl-2H-1-benzopyran-7-ol

HRID 262137

반응식

HRID 262137 반응식
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Mg].[CH3:9][C:10]1([CH3:22])[CH2:19][C:18](=O)[C:17]2[C:12](=[CH:13][C:14]([OH:21])=[CH:15][CH:16]=2)[O:11]1.[Cl-].[NH4+]>O1CCCC1>[CH3:9][C:10]1([CH3:22])[CH:19]=[C:18]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:17]2[C:12](=[CH:13][C:14]([OH:21])=[CH:15][CH:16]=2)[O:11]1

참가 물질

6

반응물 4

HCID 7961BromobenzeneHCID 25517Ammonium ChlorideHCID 6009027-hydroxy-2,2-dimethyl-3,4-dihydro-2H-1-benzopyran-4-oneHCID 5462224Magnesium

생성물 1

HCID 205704922,2-Dimethyl-4-phenyl-2H-1-benzopyran-7-ol수율 57.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

Bromobenzene (141.3 g) in dry tethydrofuran (300 ml) was added to magnesium (23.7 g) in dry tetrahydrofuran (100 ml). 2,2-Dimethylchroman-4-one-7-ol (34.5 g) in dry tetrahydrofuran (250 ml) was then added and the solution refluxed for 48 hours. The mixture was poured into ammonium chloride solution, the tetrahydrofuran layer was separated and evaporated under reduced pressure. The aqueous layer was extracted with ethyl acetate and the organic layer and the residue from the tetrahydrofuran layer was shaken with 10% sodium hydroxide solution. The basic layer was acidified and re-extracted with ethyl acetate. The organic layers were dried (MgSO4). Removal of the solvent under reduced pressure gave an oil (26 g) which was chromatographed on silica. Elution with ether-petrol (1:1) gave the title compound (14 g).

후처리

  1. temperaturethe solution refluxed for 48 hours
  2. customthe tetrahydrofuran layer was separated
  3. customevaporated under reduced pressure
  4. extractionThe aqueous layer was extracted with ethyl acetate
  5. extractionre-extracted with ethyl acetate
  6. dry with materialThe organic layers were dried (MgSO4)
  7. customRemoval of the solvent under reduced pressure

출처 및 근거

ORD 기록
ord-fdaec40753ab4971b8e70ed77e6649c0
출처 데이터셋
uspto-grants-1979_05
특허 번호
US04153617

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