2,5-Dimethoxytetrahydrofuran → HCID 10354786, compound

HRID 414706Notes

Reaction equation

HRID 414706 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[NH2:9].CO[CH:18]1[CH2:22][CH2:21][CH:20](OC)O1>C(O)(=O)C>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[N:9]1[CH:18]=[CH:22][CH:21]=[CH:20]1

Participants

4

Reactant 2

HCID 790982,5-DimethoxytetrahydrofuranHCID 10954601HCID 10954601, compound

Product 1

HCID 10354786HCID 10354786, compoundYield 69.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To 100 ml of cooled (0° C.) acetic acid was added α-(2-fluorophenyl)benzenemethanamine (13.09 g). This mixture was then brought to room temperature and 2,5-dimethoxytetrahydrofuran (8.60 g) was added dropwise. The mixture was heated at reflux for 1.5 hours, after which time TLC (thin layer chromatography) showed absence of amine. The mixture was cooled and most of the acetic acid was removed by evaporation. The mixture was dissolved in ether and washed (3×H2O; 1×sat. NaHCO3), dried (sat. NaCl and anhydrous MgSO4), filtered and concentrated to yield a brown solid. Distillation (117° [email protected] mmHg) gave a slightly yellow solid (11.33 g). A sample was recrystallized from acetonitrile to give a white crystal, mp 81°-82.5° C.

Workup

  1. customwas then brought to room temperature
  2. temperatureThe mixture was heated
  3. temperatureat reflux for 1.5 hours
  4. customwas removed by evaporation
  5. dissolutionThe mixture was dissolved in ether
  6. washwashed (3×H2O; 1×sat. NaHCO3)
  7. dry with materialdried (sat. NaCl and anhydrous MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto yield a brown solid
  11. distillationDistillation (117° [email protected] mmHg)

Sources & evidence

ORD record
ord-67f18c3ba97c436d8ce09b6b386a7469
Source dataset
uspto-grants-1988_12
Patent number
US04794110

Reaction notes

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