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

HRID 1756165Notes

Reaction equation

HRID 1756165 reaction equation
[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

Participants

13

Reactant 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

Product 1

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

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  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]

Sources & evidence

ORD record
ord-ba7a3581d02c49cc80b844aa6db8ecc2
Source dataset
uspto-grants-1995_08
Patent number
US05439932

Reaction notes

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