Tetrahydrofuran → HCID 178487746, compound

HRID 1438138Notes

Reaction equation

HRID 1438138 reaction equation
COC1C=[CH:14][C:6]([C:7]([C:9]([N:11](C)C)=N)=O)=[C:5]([CH3:16])C=1.CC(C)([O-:20])C.[K+].[CH2:23]1[CH2:27][O:26][CH2:25][CH2:24]1>>[CH3:25][O:26][C:27]1[CH:14]=[C:6]2[C:7](=[CH:24][CH:23]=1)[C:9]([OH:20])=[N:11][CH:16]=[CH:5]2

Participants

4

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 23665647Potassium tert-butoxideHCID 86606785HCID 86606785, compound

Product 1

HCID 178487746HCID 178487746, compoundYield 93.6%

Conditions

Temperature
30 °C

Procedure

A slurry of 83C (16.33 g) in a small amount of THF (25 mL) was heated to 60° C. in a flask equipped with a stir bar, reflux condenser, and addition funnel. A solution of (1 M potassium tert-butoxide in THF, 105 mL) was titrated in over a period of 30 min. The reaction turned a light yellow, and began to precipitate a solid product after about 10 min and became a thick suspension after 30 min. The reaction was cooled to 30° C. and neutralized to pH 7 with 9.5 mL conc. HCl. Water (about 25 mL) was added to dissolve all the salts, and still an easy phase split remained. The phases were split and the aqueous phase was back extracted with 25 mL ethyl acetate. The organic phases were combined and slowly concentrated at 60° C. to provide a crystalline residue. 12.16 g (93.6%) of 83D was isolated as a light orange solid. An analytical sample was prepared by recrystallization from ethyl acetate. LC retention time=13.533 min. 1H NMR (DMSO-d6) δ 3.86 (s, 3H); 6.46 (d, 1H); 7.02-7.13 (m, 3H), 8.08 (d, 1H); 11.03 (s, 1H).

Workup

  1. customequipped with a stir bar
  2. temperaturereflux
  3. additioncondenser, and addition funnel
  4. customwas titrated in over a period of 30 min
  5. customto precipitate a solid product after about 10 min
  6. customafter 30 min
  7. additionWater (about 25 mL) was added
  8. dissolutionto dissolve all the salts
  9. customstill an easy phase split
  10. customThe phases were split
  11. extractionthe aqueous phase was back extracted with 25 mL ethyl acetate
  12. concentrationslowly concentrated at 60° C.
  13. customto provide a crystalline residue

Sources & evidence

ORD record
ord-dc2f3f4cf79a43f1b771c65723c71970
Source dataset
uspto-grants-2009_11
Patent number
US07622585B2

Reaction notes

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