Hydrochloric Acid → HCID 22221637, compound

HRID 1836042Notes

Reaction equation

HRID 1836042 reaction equation
CON(C)[C:4]([C:6]1[C:14]2[O:13][C:12]([C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=3)=[CH:11][C:10]=2[CH:9]=[C:8]([O:23][CH3:24])[CH:7]=1)=[O:5].[CH3:26][Li].Cl>C1COCC1>[CH3:24][O:23][C:8]1[CH:7]=[C:6]([C:4](=[O:5])[CH3:26])[C:14]2[O:13][C:12]([C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=3)=[CH:11][C:10]=2[CH:9]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 23517383HCID 23517383, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 22221637HCID 22221637, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a cooled (−78° C.) solution of 121 (0.6 g, 1.7 mmol) in THF (10 ml) was added Methyl lithium (3.4 ml of 1.0M in THF) and the reaction was stirred for 1 hr. The solution was then poured into 2 N HCl and extracted with EtOAc which was separated, dried over MgSO4, and concentrated to give a solid which was triturated with MeOH and collected by filtration to give 122 as a white solid (0.35 g, 67%); 1H NMR (CDCl3) δ 7.78(d, 2 H, J=8.7 Hz), 7.44 (d, 1 H, 2.6 Hz), 7.24 (s, 1 H), 6.99 (d, 2 H, J=8.7 Hz), 6.89 (s, 1 H), 3.89 (s, 3 H), 3.88 (s, 3 H), 2.96 (s, 3 H).

Workup

  1. extractionextracted with EtOAc which
  2. customwas separated
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customto give a solid which
  6. customwas triturated with MeOH
  7. filtrationcollected by filtration

Sources & evidence

ORD record
ord-7909b19e4021422a80847d75bf539494
Source dataset
uspto-grants-2004_08
Patent number
US06774248B2

Reaction notes

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