1-Iodo-2,3,4-trimethoxybenzene → HCID 10384873, compound

HRID 1453994Notes

Reaction equation

HRID 1453994 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[C:4]([O:10][CH3:11])[C:3]=1[O:12][CH3:13].C([Li])CCC.[Cl:19][CH:20]1[C:29](=O)[C:28]2[C:23](=[CH:24][C:25]([N:31]([CH3:33])[CH3:32])=[CH:26][CH:27]=2)[O:22][CH2:21]1>C1COCC1>[Cl:19][C:20]1[CH2:21][O:22][C:23]2[C:28]([C:29]=1[C:7]1[CH:6]=[C:5]([O:8][CH3:9])[C:4]([O:10][CH3:11])=[C:3]([O:12][CH3:13])[CH:2]=1)=[CH:27][CH:26]=[C:25]([N:31]([CH3:33])[CH3:32])[CH:24]=2

Participants

5

Reactant 3

HCID 2569311-Iodo-2,3,4-trimethoxybenzeneHCID 57528878HCID 57528878, compoundHCID 178418339Butyllithium

Product 1

HCID 10384873HCID 10384873, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

Iodotrimethoxybenzene (40 mg, 0.133 mmol) was dissolved into 1 mL of dry THF and cooled to −78° C. The butyl lithium solution 1.16 M (126 μL, 0.146 mmol, 1.1 eq.) was added dropwise and the mixture was stirred at −78° C. for 15 min. 3-Chloro-7-dimethylamino-chroman-4-one (30 mg, 0.133 mmol) in 1 mL of dry THF was added and the mixture was allowed to warn to room temperature. After 3 h, the mixture was quenched with a saturated aqueous solution of NH4Cl (10 mL) and extracted with EtOAc (2×10 mL). Combined organic extracts were dried with Na2SO4 and concentrated. The residue was diluted in a mixture of 2 mL of ethanol and 0.75 mL of concentrated hydrochloric acid, and stirred overnight at room temperature. A saturated solution of sodium bicarbonate was added until neutralization and the resulting solution was extracted with EtOAc (2×25 mL).

Workup

  1. customto warn to room temperature
  2. waitAfter 3 h
  3. customthe mixture was quenched with a saturated aqueous solution of NH4Cl (10 mL)
  4. extractionextracted with EtOAc (2×10 mL)
  5. dry with materialCombined organic extracts were dried with Na2SO4
  6. concentrationconcentrated
  7. additionThe residue was diluted in a mixture of 2 mL of ethanol and 0.75 mL of concentrated hydrochloric acid
  8. stirringstirred overnight at room temperature
  9. additionA saturated solution of sodium bicarbonate was added until neutralization
  10. extractionthe resulting solution was extracted with EtOAc (2×25 mL)

Sources & evidence

ORD record
ord-c1601b41749a4055a28229d83905c1be
Source dataset
uspto-grants-2009_01
Patent number
US07476741B2

Reaction notes

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