2,5-Dimethoxytetrahydrofuran → HCID 57042027, compound

HRID 1464388Notes

Reaction equation

HRID 1464388 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH2:20][C:21]([O:23][CH3:24])=[O:22])[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]=1.CO[CH:27]1[CH2:31][CH2:30][CH:29](OC)O1>C(O)(=O)C>[N:1]1([C:2]2[CH:3]=[C:4]([CH2:20][C:21]([O:23][CH3:24])=[O:22])[CH:5]=[CH:6][C:7]=2[O:8][CH2:9][C:10]2[CH:19]=[CH:18][C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11]=2)[CH:27]=[CH:31][CH:30]=[CH:29]1

Participants

4

Reactant 2

HCID 790982,5-DimethoxytetrahydrofuranHCID 19087793HCID 19087793, compound

Product 1

HCID 57042027HCID 57042027, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

5 g (0.016 mmol) of the compound from Example XXIX are dissolved in 70 ml of acetic acid, 2.78 g (0.02 mol) of 2,5-dimethoxytetrahydrofuran are added and the mixture is heated to boiling for 2 hours. After distilling off the acetic acid in vacuo, taking up the residue in 200 ml of dichloromethane, extracting with water, drying with sodium sulphate and concentrating in vacuo to a small volume, the brown oil which remains (6 g) is separated by column chromatography (silica gel 60, eluent: toluene/ethyl acetate=4:1).

Workup

  1. temperaturethe mixture is heated
  2. distillationAfter distilling off the acetic acid in vacuo
  3. extractionextracting with water
  4. dry with materialdrying with sodium sulphate
  5. concentrationconcentrating in vacuo to a small volume
  6. customis separated by column chromatography (silica gel 60, eluent: toluene/ethyl acetate=4:1)

Sources & evidence

ORD record
ord-022796c64f69491580764133a5b436d0
Source dataset
uspto-grants-1994_04
Patent number
US05304563

Reaction notes

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