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Dichloromethane → 5-Methyl-4-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenylsulphanylmethyl]-furan-2-carboxylic acid methyl ester

HRID 460096
ノート
印刷プレビュー

反応式

HRID 460096 の反応式
ClCCl.[CH3:4][C:5]1([CH3:12])[C:9]([CH3:11])([CH3:10])[O:8][BH:7][O:6]1.[CH3:13][O:14][C:15]([C:17]1[O:18][C:19]([CH3:31])=[C:20]([CH2:22][S:23][C:24]2[CH:29]=[CH:28][C:27](Br)=[CH:26][CH:25]=2)[CH:21]=1)=[O:16]>O1CCCC1.O1CCOCC1>[CH3:13][O:14][C:15]([C:17]1[O:18][C:19]([CH3:31])=[C:20]([CH2:22][S:23][C:24]2[CH:29]=[CH:28][C:27]([B:7]3[O:8][C:9]([CH3:11])([CH3:10])[C:5]([CH3:12])([CH3:4])[O:6]3)=[CH:26][CH:25]=2)[CH:21]=1)=[O:16]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 6344DichloromethaneHCID 27347684,4,5,5-Tetramethyl[1,3,2]dioxaborolaneHCID 588241724-(4-Bromo-phenylsulphanylmethyl)-5-methyl-furan-2-carboxylic acid methyl ester

生成物 1

HCID 588241845-Methyl-4-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenylsulphanylmethyl]-furan-2-carboxylic acid methyl ester

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran
溶媒
HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

[1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium(II) complex with dichloromethane (1:1) (30 mg) and 4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (2.34 ml of a 1M solution in tetrahydrofuran) were added to a degassed solution of 4-(4-bromo-phenylsulphanylmethyl)-5-methyl-furan-2-carboxylic acid methyl ester (150) (400 mg, 1.17 mmoles) in 1,4-dioxan (120 ml). The mixture was heated at 100° C., under an argon atmosphere, for 20 hours, cooled and evaporated. The residue was partitioned between ethyl acetate and water, and the organic phase washed with brine and dried (MgSO4). After evaporation of the solvent the residue was purified by by flash chromatography, using heptane/ethyl acetate 9:1v/v as eluent, to afford compound 151(212 mg) as a colourless oil.

後処理

  1. temperaturecooled
  2. customevaporated
  3. customThe residue was partitioned between ethyl acetate and water
  4. washthe organic phase washed with brine
  5. dry with materialdried (MgSO4)
  6. customAfter evaporation of the solvent the residue
  7. customwas purified by by flash chromatography

出典と根拠

ORDレコード
ord-3b046694638e47d6b9452992e4ef3b04
出典データセット
uspto-grants-2007_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07196089B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート