2,5-Dimethoxytetrahydrofuran → HCID 58551015, compound

HRID 1908042Notes

Reaction equation

HRID 1908042 reaction equation
[NH2:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[OH:9].CO[CH:12]1[CH2:16][CH2:15][CH:14](OC)O1>C(O)(=O)C>[CH3:8][C:7]1[C:2]([N:1]2[CH:12]=[CH:16][CH:15]=[CH:14]2)=[C:3]([OH:9])[CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 790982,5-DimethoxytetrahydrofuranHCID 30141382-Amino-m-cresol

Product 1

HCID 58551015HCID 58551015, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

A round bottom flask was charged with 2-amino-3-methyl-phenol (2.5 g, 20.3 mmol) and acetic acid (37.5 mL) which provided a very dark solution. Stirring was commenced and the vessel was charged with 2,5-dimethoxytetrahydrofuran (2.6 mL, 20.3 mmol) added neat dropwise over a period of 2 minutes. The dark mixture was then heated at 100° C. for 3 h then 80° C. for 12 hours. The solvent was evaporated under vacuum and the crude residue purified by column chromatography using a gradient of 0.5-50% EtOAc in hexanes to yield 3-methyl-2-(1H-pyrrol-1-yl)phenol (2.9 g, 83%). ESI-MS m/z calc. 173.1. found 174.3 (M+1)+. Retention time: 1.31 minutes (3 min run).

Workup

  1. customprovided a very dark solution
  2. additionadded neat dropwise over a period of 2 minutes
  3. customThe solvent was evaporated under vacuum
  4. customthe crude residue purified by column chromatography

Sources & evidence

ORD record
ord-99bda6c1ef41415094f98d5bbba208c9
Source dataset
uspto-grants-2013_12
Patent number
US08598164B2

Reaction notes

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