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1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 57706034、化合物

HRID 1662323
ノート
印刷プレビュー

反応式

HRID 1662323 の反応式
[Cl-].[Li+].C[C:4](P(OC)(O)=O)([C:6]([O-:8])=[O:7])C.[CH2:14]1CCN2C(=NCCC2)CC1.[F:25][C:26]([F:38])([F:37])[C:27]([C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([O:35][CH3:36])[CH:30]=1)=O>CC#N>[F:25][C:26]([F:38])([F:37])/[C:27](/[C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([O:35][CH3:36])[CH:30]=1)=[CH:4]\[C:6]([O:8][CH3:14])=[O:7]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 433294Lithium ChlorideHCID 27597342,2,2-Trifluoro-1-(3-methoxyphenyl)ethanoneHCID 53413272Trimethylphosphonoacetate

生成物 1

HCID 57706034HCID 57706034、化合物収率 97.7%

試薬・触媒・溶媒 1

HCID 6342
Acetonitrile
溶媒

実験手順

To a suspension of lithium chloride (0.623 g, 14.7 mmol) in MeCN (20 mL), were added trimethylphosphonoacetate (available from Aldrich) (1.70 mL, 11.8 mmol), DBU (1.76 mL, 11.8 mmol), and 2,2,2-trifluoro-1-(3-methoxyphenyl)ethanone (available from Oakwood Products Inc.) (2.0 g, 9.80 mmol) at room temperature. The pale yellow mixture was heated to reflux and stirred overnight. The mixture was partitioned between water and EtOAc. The layers were separated, and the aqueous phase was extracted with additional EtOAc. The combined organic layers were washed with 1 N HCl and brine, dried over Na2SO4, and concentrated. The crude product was purified by silica gel flash chromatography (0-10% EtOAc/hexane) to afford 6.1 (2.49 g, 97.7% yield) as a colorless oil.

後処理

  1. temperatureThe pale yellow mixture was heated
  2. temperatureto reflux
  3. customThe mixture was partitioned between water and EtOAc
  4. customThe layers were separated
  5. extractionthe aqueous phase was extracted with additional EtOAc
  6. washThe combined organic layers were washed with 1 N HCl and brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated
  9. customThe crude product was purified by silica gel flash chromatography (0-10% EtOAc/hexane)

出典と根拠

ORDレコード
ord-5c3f9f4993e64b80bcf5d11727a5999f
出典データセット
uspto-grants-2011_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08030354B2

反応ノート

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