Hydrochloric Acid → Ethyl [6,7-dichloro-1-oxo-2-phenyl-2-(3-(trimethylsilyl)-2-propynyl)-5-indanyloxy]acetate

HRID 1578172ノート

反応式

HRID 1578172 の反応式
Br[CH2:2][C:3]#[C:4][Si:5]([CH3:8])([CH3:7])[CH3:6].[Cl:9][C:10]1[C:18]([Cl:19])=[C:17]2[C:13]([CH2:14][CH:15]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:16]2=[O:20])=[CH:12][C:11]=1[O:27][CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30].C(=O)([O-])[O-].[K+].[K+].Cl>CCOCC.CN(C)C=O>[Cl:9][C:10]1[C:18]([Cl:19])=[C:17]2[C:13]([CH2:14][C:15]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)([CH2:2][C:3]#[C:4][Si:5]([CH3:8])([CH3:7])[CH3:6])[C:16]2=[O:20])=[CH:12][C:11]=1[O:27][CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 6425893-Bromo-1-(trimethylsilyl)-1-propyneHCID 12774090Ethyl (6,7-dichloro-1-oxo-2-phenyl-5-indanyloxy)acetate

生成物 1

HCID 12774091Ethyl [6,7-dichloro-1-oxo-2-phenyl-2-(3-(trimethylsilyl)-2-propynyl)-5-indanyloxy]acetate収率 87%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 6228Dimethylformamide溶媒

実験手順

A solution of 1-bromo-3-(trimethylsilyl)-2-propyne (2.87 g., 15.0 mmol) prepared according to methods of Corey, Tet. Lett., 3963 (1973) and Miller, Syn. Comun., 2, 267 (1972) in 50 ml. of dimethylformamide is added to a mixture of ethyl (6,7-dichloro-1-oxo-2-phenyl-5-indanyloxy)acetate (2.9 g., 7.65 mmol) and powdered potassium carbonate (2.65 g., 19.2 mmol) under an argon atmosphere. After stirring at 60° for a period of 2 hr. and cooling to room temperature, ether is added to the reaction mixture followed by dilute hydrochloric acid. The acidified solution is extracted with ether and the ethereal extract sequentially washed with water and brine, and then dried over magnesium sulfate. Removal of solvent under reduced pressure affords 4.72 g. of tan solid. Crystallization of this material from cyclohexane provides 3.26 g., (87% yield) of ethyl [6,7-dichloro-1-oxo-2-phenyl-2-(3-(trimethylsilyl)-2-propynyl)-5-indanyloxy]acetate, m.p. 111.5°- 113° (corr.).

後処理

  1. extractionThe acidified solution is extracted with ether
  2. extractionthe ethereal extract sequentially
  3. washwashed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customRemoval of solvent under reduced pressure
  6. customaffords 4.72 g
  7. customCrystallization of this material from cyclohexane
  8. customprovides 3.26 g

出典と根拠

ORDレコード
ord-5a532f3fcc6f49a9829a2da8097ac01b
出典データセット
uspto-grants-1981_09
特許番号
US04291168

反応ノート

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