Tributylvinyltin → 7-chloro-4-(4-fluorophenyl)-2,2-dimethyl-3-vinyl-2H-chromen

HRID 1959132ノート

反応式

HRID 1959132 の反応式
Br[C:2]1[C:3]([CH3:21])([CH3:20])[O:4][C:5]2[C:10]([C:11]=1[C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=1)=[CH:9][CH:8]=[C:7]([Cl:19])[CH:6]=2.[CH2:22]([Sn](CCCC)(CCCC)C=C)[CH2:23]CC.[F-].[K+]>O1CCOCC1.C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:19][C:7]1[CH:6]=[C:5]2[C:10]([C:11]([C:12]3[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=3)=[C:2]([CH:22]=[CH2:23])[C:3]([CH3:21])([CH3:20])[O:4]2)=[CH:9][CH:8]=1

参加物

7

反応物 3

HCID 81998TributylvinyltinHCID 522689Potassium FluorideHCID 59443055HCID 59443055、化合物

生成物 1

HCID 594429667-chloro-4-(4-fluorophenyl)-2,2-dimethyl-3-vinyl-2H-chromen

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 8857Ethyl Acetate溶媒HCID 312751,4-Dioxane溶媒

実験手順

A mixture of 3-bromo-7-chloro-4-(4-fluorophenyl)-2,2-dimethyl-2H-chromen (a compound obtained in Reference Example 8(1); 220 mg), tributyl(vinyl)tin (350 μL) and tetrakis(triphenylphosphine)palladium(0) (140 mg) in dioxane was heated under reflux for 23 hours. After cooling, the reaction solution was diluted with ethyl acetate, a saturated aqueous solution of potassium fluoride was added thereto, and the mixture was stirred at room temperature for an hour. The reaction solution was filtered through Celite and the filtrate was extracted with ethyl acetate. The organic layer was washed successively with water and brine, filtered through a column of porous diatomite (Chem Elut) and the filtrate was concentrated in vacuo. The resultant residue was purified by column chromatography on silica gel (Solvent: n-hexane/chloroform=100/0 to 95/5) to give the titled compound (157 mg) as a pale yellow viscous oil.

後処理

  1. customobtained in Reference Example 8(1)
  2. temperatureunder reflux for 23 hours
  3. temperatureAfter cooling
  4. filtrationThe reaction solution was filtered through Celite
  5. extractionthe filtrate was extracted with ethyl acetate
  6. washThe organic layer was washed successively with water and brine
  7. filtrationfiltered through a column of porous diatomite (Chem Elut)
  8. concentrationthe filtrate was concentrated in vacuo
  9. customThe resultant residue was purified by column chromatography on silica gel (Solvent: n-hexane/chloroform=100/0 to 95/5)

出典と根拠

ORDレコード
ord-a188d2210c9a448e9f93bb0d864559e6
出典データセット
uspto-grants-2013_04
特許番号
US08410166B2

反応ノート

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