Hydrochloric Acid → HCID 11380123、化合物

HRID 2425043ノート

反応式

HRID 2425043 の反応式
C([Si](Cl)(CC)CC)C.Br[C:10]([Br:17])([F:16])[C:11]([O:13][CH2:14][CH3:15])=[O:12].[C:18]1(=[O:23])[CH2:22][CH2:21][CH:20]=[CH:19]1.Cl>C(#N)C.[Zn].CCOC(C)=O>[Br:17][C:10]([F:16])([CH:20]1[CH2:21][CH2:22][C:18](=[O:23])[CH2:19]1)[C:11]([O:13][CH2:14][CH3:15])=[O:12]

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 135882-Cyclopenten-1-oneHCID 13819ChlorotriethylsilaneHCID 2737168Ethyl 2,2-dibromo-2-fluoroacetate

生成物 1

HCID 11380123HCID 11380123、化合物収率 88%

試薬・触媒・溶媒 3

HCID 23994Zinc触媒HCID 6342Acetonitrile溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Add 8.45 mL (50.4 mmol) of triethylsilyl chloride to a suspension of 2.99 g of activated Zn (45.8 mmol) in anhydrous acetonitrile (100 mL) at −20° C. and stir the mixture for 5 minutes. Add 8.0 mL (57.3 mmol) of ethyl 2,2-dibromo-2-fluoracetate and stir the mixture for 90 minutes at −20° C. Add 1.86 mL (22.9 mmol) of 2-cyclopenten-1-one, and stir the reaction mixture overnight, allowing the temperature to rise slowly to room temperature. Add HCl 1N (125 mL) and EtOAc (100 mL). Wash the organic layer with saturated NaHCO3 (2×150 mL), water (2×150 mL) and brine (2×150 mL), dry over anhydrous MgSO4, filter and concentrate under reduced pressure. Purify the residue by column chromatography using EtOAc/hexane (1:8) as eluent to give the title compound (5.36 g, 88% overall yield) as a colorless oil as a mixture of diastereoisomers.

後処理

  1. stirringstir the mixture for 90 minutes at −20° C
  2. stirringstir the reaction mixture overnight
  3. customto rise slowly to room temperature
  4. washWash the organic layer with saturated NaHCO3 (2×150 mL), water (2×150 mL) and brine (2×150 mL)
  5. dry with materialdry over anhydrous MgSO4
  6. filtrationfilter
  7. concentrationconcentrate under reduced pressure
  8. customPurify the residue by column chromatography

出典と根拠

ORDレコード
ord-6822f75de1de42c3b711b8979bc8e151
出典データセット
uspto-grants-2011_06
特許番号
US07964632B2

反応ノート

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