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Vinyl Acetate → 1-[4-Hydroxy-3-(hydroxymethyl)-1-butyl]-5-vinyluracil

HRID 1516772
ノート
印刷プレビュー

反応式

HRID 1516772 の反応式
[C:1]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C[CH:2]=1.[OH-].[Ca+2].[OH-].[OH:23][CH2:24][CH:25]([CH2:37][OH:38])[CH2:26][CH2:27][N:28]1[CH:35]=[C:34](I)[C:32](=[O:33])[NH:31][C:29]1=[O:30].C(OC=C)(=O)C>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(N(CC)CC)C>[OH:23][CH2:24][CH:25]([CH2:37][OH:38])[CH2:26][CH2:27][N:28]1[CH:35]=[C:34]([CH:1]=[CH2:2])[C:32](=[O:33])[NH:31][C:29]1=[O:30]
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

8

反応物 4

HCID 7904Vinyl AcetateHCID 11776TriphenylphosphineHCID 6093208Calcium HydroxideHCID 578389821-[4-Hydroxy-3-(hydroxymethyl)-1-butyl]-5-iodouracil

生成物 1

HCID 100372831-[4-Hydroxy-3-(hydroxymethyl)-1-butyl]-5-vinyluracil収率 475.7%

試薬・触媒・溶媒 3

HCID 167845
palladium(II) acetate
触媒
HCID 6228Dimethylformamide溶媒
HCID 8471Triethylamine溶媒

反応条件

温度
70 °C

実験手順

A mixture of palladium (II) acetate (79 mg, 0.35 mmol), triphenylphosphine (185 mg, 0.7 mmol) and triethylamine (5 ml), (dried over calcium hydroxide) in dry DMF (80 ml) was maintained at 70° C. with stirring until an intense red color appeared. Compound 19 (2.36 gm, 6.95 mmol) and vinyl acetate (30 ml, 330 mmol) were then added, and the reaction was allowed to proceed at 70° C. for 6 h with stirring. The solvent was removed in vacuo and the residue obtained was extracted with water (2×50 ml). The water layer was washed with dichloromethane, evaporated in vacuo, and the residue obtained was purified by elution from a silica gel column using ethyl acetate-methanol (95:5, v/v) as eluent to give 20 as a viscous oil (800 mg, 48%).

後処理

  1. stirringwith stirring
  2. customThe solvent was removed in vacuo
  3. customthe residue obtained
  4. extractionwas extracted with water (2×50 ml)
  5. washThe water layer was washed with dichloromethane
  6. customevaporated in vacuo
  7. customthe residue obtained
  8. customwas purified by elution from a silica gel column

出典と根拠

ORDレコード
ord-bcadf2594cd346e8baa5b1374bea1ba2
出典データセット
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08227594B2

反応ノート

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