Nitrogen → Methyl (5-fluoro-2-methyl-1H-inden-3-yl)acetate

HRID 567192Notes

Reaction equation

HRID 567192 reaction equation
N(CN[C:5](N)=[O:6])=O.[OH-].[K+].[F:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[CH2:16][C:15]([CH3:20])=[C:14]2[CH2:21][C:22](O)=[O:23].N#N>ClCCl.C(OCC)C>[F:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[CH2:16][C:15]([CH3:20])=[C:14]2[CH2:21][C:22]([O:6][CH3:5])=[O:23]

Participants

7

Reactant 4

HCID 947NitrogenHCID 14797Potassium HydroxideHCID 104823Urea, (nitrosomethyl)-HCID 30156085-Fluoro-2-methyl-1H-indene-3-acetic acid

Product 1

HCID 15434585Methyl (5-fluoro-2-methyl-1H-inden-3-yl)acetateYield 93%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

Nitrosomethylurea (99.5 mmol) is added in portions to a cold (0° C.) mixture of aqueous 50% KOH (50 ml) and diethylether (150 ml) at 0° C. The yellow ether solution of diazomethane (Note: explosive) is separated, is washed with water, and is added in portions to a solution of 5-fluoro-2-methylindene-3-acetic acid (90 mmol) in dichloromethane (200 ml). When the evolution of N2 ceases, the reaction is complete. After evaporation of the solvents, the residue is recrystallized from hexane to give methyl 5-fluoro-2-methyl-3-indenylacetate (yield 93%; m.p. 53° C.).

Workup

  1. customThe yellow ether solution of diazomethane (Note: explosive) is separated
  2. washis washed with water
  3. customAfter evaporation of the solvents
  4. customthe residue is recrystallized from hexane

Sources & evidence

ORD record
ord-640f6b0c2e5e4c86baabf1baee723f27
Source dataset
uspto-grants-2001_01
Patent number
US06177471B1

Reaction notes

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