Hydrochloric Acid → HCID 66584683, compound

HRID 540654Notes

Reaction equation

HRID 540654 reaction equation
C([Li])CCC.[CH3:6][O:7][C:8]1[C:20]2[CH:19]=[CH:18][O:17][C:16]=2[C:15]([O:21][CH3:22])=[C:14]2[C:9]=1[CH:10]=[CH:11][CH:12]=[CH:13]2.CN(C)C=[O:26].Cl>O1CCCC1>[O:26]=[C:18]1[O:17][C:16]2[C:15]([O:21][CH3:22])=[C:14]3[C:9](=[C:8]([O:7][CH3:6])[C:20]=2[CH2:19]1)[CH:10]=[CH:11][CH:12]=[CH:13]3

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 10704532HCID 10704532, compoundHCID 178418339Butyllithium

Product 1

HCID 66584683HCID 66584683, compoundYield 76.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 5.5 mL (12.28 mmoles) of 2.2 M n-butyl lithium diluted with 20 mL of anhydrous tetrahydrofuran in an ice bath, 1.4 gram (6.14 mmoles) of 4,9-dimethoxy-naphtho[2,3-b]furan in 20 mL of anhydrous tetrahydrofuran was added dropwise over 5 minutes. The mixture was further stirred for 40 minutes in ice bath, and then 0.95 mL (12.28 mmoles) of N,N-dimethylformamide was added dropwise over 5 minutes. The mixture was stirred for additional 30 minutes in ice bath, and then further stirred for 120 minutes at room temperature. The reaction mixture was stopped by addition of 100 mL 0.1N hydrochloric acid, and then evaporated to remove tetrahydrofuran. The remaining aqueous solution was extracted with dichloromethane twice. The combined organic phase was washed with water, dried with anhydrous sodium sulfate, and evaporated to dryness. Product was purified by silica gel chromatograph using dichloromethane as elution solvent. 1.20 gram (4.69 mmoles) of product was obtained with yield of 76% and characterized by 1H NMR and mass spectrum. 1H NMR (in CDCl3) δ 4.30 (s, 3H), 4.34 (s, 3H), 7.47-7.51 (m, 1H), 7.55-7.59 (m, 1H), 7.89 (s, 1H), 8.29-8.33 (m, 2H), 9.95 (s, 1H). Mass (M+H) is 257.

Workup

  1. stirringThe mixture was stirred for additional 30 minutes in ice bath
  2. stirringfurther stirred for 120 minutes at room temperature
  3. customevaporated
  4. customto remove tetrahydrofuran
  5. extractionThe remaining aqueous solution was extracted with dichloromethane twice
  6. washThe combined organic phase was washed with water
  7. dry with materialdried with anhydrous sodium sulfate
  8. customevaporated to dryness
  9. customProduct was purified by silica gel chromatograph
  10. washas elution solvent

Sources & evidence

ORD record
ord-6d2d83cafc0e4cecb2d6913cef956917
Source dataset
uspto-grants-2014_10
Patent number
US08871802B2

Reaction notes

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