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

HRID 732923
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인쇄 미리보기

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HRID 732923 반응식
[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]
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참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 167845
palladium(II) acetate
촉매
HCID 6228Dimethylformamide용매
HCID 8471Triethylamine용매

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온도
70 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-802df62062a34b8e9fb92d9159a30587
출처 데이터셋
uspto-grants-2009_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07589077B2

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