Triethylsilane → HCID 18472193、化合物

HRID 2228215ノート

反応式

HRID 2228215 の反応式
O=CCCCC([O-])=O.C([SiH](CC)CC)C.C(=O)(O)[O-].[Na+].[CH3:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]2[S:32][C:31]([CH2:33][CH2:34][CH2:35][CH2:36][C:37]([O:39]CC)=[O:38])=[CH:30][CH:29]=2)=[CH:24][CH:23]=1.[OH-].[Na+]>FC(F)(F)C(O)=O.O1CCCC1.O.C(OCC)(=O)C>[CH3:21][C:22]1[CH:23]=[CH:24][C:25]([C:28]2[S:32][C:31]([CH2:33][CH2:34][CH2:35][CH2:36][C:37]([OH:39])=[O:38])=[CH:30][CH:29]=2)=[CH:26][CH:27]=1

参加物

10

反応物 5

HCID 12052TriethylsilaneHCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 9548601HCID 9548601、化合物HCID 18472605HCID 18472605、化合物

生成物 1

HCID 18472193HCID 18472193、化合物

試薬・触媒・溶媒 4

HCID 962Water溶媒HCID 6422Trifluoroacetic acid溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of ethyl 5-5—(4-methylphenyl) thiophen-2-yl]-5-oxovalerate (4.50 g) in trifluoroacetic acid (7.66 ml) was added triethylsilane(5.7 ml) at room temperature, and the mixture was stirred for 4 days. To the reaction mixture was added ethyl acetate, and the mixture was made alkaline with saturated sodium bicarbonate solution. The organic layer was washed with saturated sodium chloride solution, dried with magnesium sulfate and concentrated under reduced pressure. The residue was separated and purified with column chromatography (ethyl acetate/hexane=1:9) to give crude ethyl 5-[5—(4-methylphenyl)thiophen-2-yl]valerate. To a solution of the crude ethyl 5-[5—(4-methylphenyl)thiophen-2-yl]valerate in tetrahydrofuran (50 ml) was added 1N sodium hydroxide (20 ml) at room temperature, and the mixture was stirred for 24 hours. To the reaction mixture was added water, and the mixture was washed with diethylether. The aqueous layer was acidified with 1N hydrochloric acid, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride solution, dried with magnesium sulfate and concentrated under reduced pressure to precipitate crystals, which were collected by filtration and washed with hexane to give 5-[5—(4-methylphenyl)-thiophen-2-yl]valeric acid (2.88 g) as colorless crystals.

後処理

  1. washThe organic layer was washed with saturated sodium chloride solution
  2. dry with materialdried with magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was separated
  5. custompurified with column chromatography (ethyl acetate/hexane=1:9)
  6. customto give crude ethyl 5-[5—(4-methylphenyl)thiophen-2-yl]valerate
  7. stirringthe mixture was stirred for 24 hours
  8. washthe mixture was washed with diethylether
  9. extractionthe mixture was extracted with ethyl acetate
  10. washThe organic layer was washed with saturated sodium chloride solution
  11. dry with materialdried with magnesium sulfate
  12. concentrationconcentrated under reduced pressure
  13. customto precipitate crystals, which
  14. filtrationwere collected by filtration
  15. washwashed with hexane

出典と根拠

ORDレコード
ord-8994d687609b4244ab4c513f505d7285
出典データセット
uspto-grants-2002_07
特許番号
US06413947B1

反応ノート

読み込み中…