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

HRID 1390136노트

반응식

HRID 1390136 반응식
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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 6228Dimethylformamide용매

실험 절차

- 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.).

후처리

  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

출처 및 근거

ORD 기록
ord-61974803002c4cf5b6c72ec51d7e6f9c
출처 데이터셋
uspto-grants-1981_01
특허 번호
US04247715

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