Dimethylformamide → HCID 86754437, compound

HRID 1586609Notes

Reaction equation

HRID 1586609 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]2[CH2:10][CH:9]2[C:11]2[S:12][CH:13]=[CH:14][CH:15]=2)[CH:5]=[CH:6][CH:7]=1.CN(C)C=O.[OH-].[Na+].[CH3:23][O:24]/[N:25]=[C:26](\[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[CH2:37]Br)/[C:27]([O:29][CH3:30])=[O:28]>O>[S:12]1[CH:13]=[CH:14][CH:15]=[C:11]1[CH:9]1[CH2:10][CH:8]1[C:4]1[CH:3]=[C:2]([CH:7]=[CH:6][CH:5]=1)[O:1][CH2:37][C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=1[C:26](=[N:25][O:24][CH3:23])[C:27]([O:29][CH3:30])=[O:28]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 10989774(E)-Methyl 2-(methoxyimino)-2-[2-(bromomethyl)phenyl]acetateHCID 21217141HCID 21217141, compound

Product 1

HCID 86754437HCID 86754437, compoundYield 86.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 20 ml glass vial equipped with a magnetic stirring bar was charged 2.2 g (0.0102 moles) of 1-(3-hydroxyphenyl)-2-(2-thienyl)cyclopropane, 15 mls of dry N,N-dimethylformamide, and 0.41 g (0.0102 moles) of powdered sodium hydroxide. To this solution was added 2.9 g (0.0102 moles) of methyl (E)-2-(bromomethyl)phenylglyoxylate O-methyloxime in one portion. The vial was capped and stirred overnight at ambient temperature. The reaction mixture was then poured into 100 mls of water, and extracted with s×100 mls of ethyl ether. The ether extract was then washed with 2×100 mls of water and 100 mls of saturated aqueous sodium chloride solution. The ether extract was then dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure with a rotary evaporator at 45° C. to afford 5.1 g of the crude product as an dark green oil. This material was chromatographed on a mixed bed of neutral alumina and silica gel with 50% ethyl acetate, 50% hexane. The pure fractions were combined, and concentrated under reduced pressure with a rotary evaporator to afford 3.7 g of the title compound, Methyl2-[2-((3-(2-(thien-2-yl)cyclopropyl))phenoxymethyl)phenyl]-2-methoxyiminoacetate as a viscous yellow oil. 86% isolated yield.

Workup

  1. customThe vial was capped
  2. extractionextracted with s×100 mls of ethyl ether
  3. extractionThe ether extract
  4. washwas then washed with 2×100 mls of water and 100 mls of saturated aqueous sodium chloride solution
  5. extractionThe ether extract
  6. dry with materialwas then dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure with a rotary evaporator at 45° C.
  9. customto afford 5.1 g of the crude product as an dark green oil
  10. customThis material was chromatographed on a mixed bed of neutral alumina and silica gel with 50% ethyl acetate, 50% hexane
  11. concentrationconcentrated under reduced pressure with a rotary evaporator

Sources & evidence

ORD record
ord-7c4aee6c07ae4c27a7c84044334a2dc6
Source dataset
uspto-grants-1999_08
Patent number
US05945557

Reaction notes

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