Ethyl bromoacetate → Methyl [1-methyl-2-[3-(3-thienyl)phenoxy]ethoxy]acetate

HRID 1464774노트

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HRID 1464774 반응식
[S:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:7]=[C:8]([CH:14]=[CH:15][CH:16]=2)[O:9][CH2:10][CH:11]([OH:13])[CH3:12])=[CH:2]1.S1C=CC(C2C=C(C=CC=2)OCC(=O)C)=C1.S1C=CC(C2C=C(O)C=CC=2)=C1.BrCC(=O)C.C(=O)([O-])[O-].[K+].[K+].[BH4-].[Na+].[H-].[Na+].Br[CH2:61][C:62]([O:64][CH2:65]C)=[O:63]>C(O)C.CN(C)C=O.O.C(OCC)C>[CH3:12][CH:11]([O:13][CH2:61][C:62]([O:64][CH3:65])=[O:63])[CH2:10][O:9][C:8]1[CH:14]=[CH:15][CH:16]=[C:6]([C:3]2[CH:4]=[CH:5][S:1][CH:2]=2)[CH:7]=1

참가 물질

13

반응물 8

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 11715BromoacetoneHCID 24758Sodium hydrideHCID 41303433-(Thiophen-3-YL)phenolHCID 4311764Sodium borohydrideHCID 199171261-[3-(3-Thienyl)phenoxy]-2-propanolHCID 199171563-(3-Thienyl)phenoxyacetone

생성물 1

HCID 53730012Methyl [1-methyl-2-[3-(3-thienyl)phenoxy]ethoxy]acetate

시약·촉매·용매 4

HCID 702Ethanol용매HCID 962Water용매HCID 3283Diethyl Ether용매HCID 6228Dimethylformamide용매

실험 절차

0.68 g of 1-[3-(3-thienyl)phenoxy]-2-propanol [synthesized by reducing 3-(3-thienyl)phenoxyacetone, prepared by the reaction of 3-(3-thienyl)phenol and monobromoacetone in the presence of potassium carbonate, with sodium borohydride in ethanol] was dissolved in 7 ml of dimethylformamide, and 48 mg of 60% oily sodium hydride was added. After the mixture was stirred at room temperature for 20 minutes, 0.12 ml of ethyl bromoacetate was added. The mixture was stirred at room temperature for 2 hours, and then ethyl ether and water were added. The organic layer separated was worked up in a customary manner, and the product was purified by silica gel column chromatography [hexane / ethyl acetate=10/1] to give 0.12 g of methyl [1-methyl-2-[3-(3-thienyl)phenoxy]ethoxy]acetate as a colorless oil.

후처리

  1. stirringThe mixture was stirred at room temperature for 2 hours
  2. customThe organic layer separated
  3. customthe product was purified by silica gel column chromatography [hexane / ethyl acetate=10/1]

출처 및 근거

ORD 기록
ord-89ff3ddf0ed8455b9017e2af27830d44
출처 데이터셋
uspto-grants-1994_04
특허 번호
US05306728

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