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Stannane, tributyl(1-ethoxyethenyl)- → 1-{4-Fluoro-3-[hydroxy(phenyl)methyl]phenyl}ethanone

HRID 1365065
ノート
印刷プレビュー

反応式

HRID 1365065 の反応式
Br[C:2]1[CH:3]=[CH:4][C:5]([F:16])=[C:6]([CH:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[OH:9])[CH:7]=1.C([Sn](CCCC)(CCCC)[C:22]([O:24]CC)=[CH2:23])CCC>[Cl-].C([N+](CC)(CC)CC)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(#N)C>[F:16][C:5]1[CH:4]=[CH:3][C:2]([C:22](=[O:24])[CH3:23])=[CH:7][C:6]=1[CH:8]([OH:9])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1
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 2

HCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 54595143HCID 54595143、化合物

生成物 1

HCID 577324311-{4-Fluoro-3-[hydroxy(phenyl)methyl]phenyl}ethanone

試薬・触媒・溶媒 3

HCID 5946Tetraethylammonium Chloride触媒HCID 178418476HCID 178418476、化合物触媒
HCID 6342
Acetonitrile
溶媒

反応条件

温度
150 °C

実験手順

A 5 mL microwave tube was charged with (5-bromo-2-fluorophenyl)-(phenyl)methanol (1 eq), tributyl-(1-ethoxyvinyl)tin (1 eq), tetraethylammonium chloride (3 eq), bis(triphenylphosphine)palladium(II) chloride (10 mol %) and acetonitrile (3.5 mL). The reaction was heated to 150° C. for one hour using microwave irradiation. The reaction was concentrated to dryness and the residue was taken up in water and extracted with ethyl acetate. The organics were dried over magnesium sulfate, filtered and then concentrated to an oil. Purification by silica gel chromatography provided 1-{4-fluoro-3-[hydroxy(phenyl)methyl]phenyl}ethanone as an oil. H1 NMR (d6-dmso): 8.16 (dd, 1H), 7.89 (m, 1H), 7.18-7.34 (m, 6H), 6.14 (d, 1H), 5.93 (d, 1H), 2.53 (s, 3H).

後処理

  1. custommicrowave irradiation
  2. concentrationThe reaction was concentrated to dryness
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organics were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to an oil
  7. customPurification by silica gel chromatography

出典と根拠

ORDレコード
ord-18d3697e92a74718b348c64d4ced7a25
出典データセット
uspto-grants-2011_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07888503B2

反応ノート

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