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

HRID 1756165ノート

反応式

HRID 1756165 の反応式
[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

参加物

13

反応物 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

生成物 1

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

試薬・触媒・溶媒 4

HCID 702Ethanol溶媒HCID 962Water溶媒HCID 3283Diethyl Ether溶媒HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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]

出典と根拠

ORDレコード
ord-ba7a3581d02c49cc80b844aa6db8ecc2
出典データセット
uspto-grants-1995_08
特許番号
US05439932

反応ノート

読み込み中…