2-Chloro-7-methoxynaphthalene-1,4-dione → HCID 13455828, compound

HRID 569231Notes

Reaction equation

HRID 569231 reaction equation
Cl[C:2]1[C:11](=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([O:13][CH3:14])[CH:9]=2)[C:4](=[O:15])[CH:3]=1>O1CCCC1>[OH:15][C:4]1[C:2]2[C:11](=[O:12])[C:10]3[C:5](=[CH:6][CH:7]=[C:8]([O:13][CH3:14])[CH:9]=3)[C:4](=[O:15])[C:3]=2[CH:11]=[C:10]2[C:5]=1[CH2:6][CH2:7][C:8](=[O:13])[CH2:9]2

Participants

3

Reactant 1

HCID 128295782-Chloro-7-methoxynaphthalene-1,4-dione

Product 1

HCID 13455828HCID 13455828, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of the keten acetal VII (2.5 g; 8.9 mmol) in tetrahydrofuran (THF) (3 ml) is added dropwise at 0° C. to a solution of 3-chloro-6-methoxy-1,4-naphthoquinone (1.9 g; 8.6 mmol) in THF (20 ml). The reaction medium is stirred overnight at ambient temperature. After evaporation of the solvent, the solid obtained is added slowly to a solution of HF (25 ml)-SbF5 (5 ml) at -40° C. in a Teflon flask. The mixture is kept at -40° C. for 20 minutes and then poured slowly into 500 ml of a water/ice mixture. After extraction with methylene chloride, the organic phase is washed with water, dried over sodium sulfate and then evaporated. The tetracyclic ketone is purified by chromatography under pressure (eluent: CH2Cl2) (1.11 g; 40%).

Workup

  1. customAfter evaporation of the solvent
  2. customthe solid obtained
  3. waitThe mixture is kept at -40° C. for 20 minutes
  4. extractionAfter extraction with methylene chloride
  5. washthe organic phase is washed with water
  6. dry with materialdried over sodium sulfate
  7. customevaporated
  8. customThe tetracyclic ketone is purified by chromatography under pressure (eluent: CH2Cl2) (1.11 g; 40%)

Sources & evidence

ORD record
ord-fd71f582541246d3b3985519e0413735
Source dataset
uspto-grants-1988_03
Patent number
US04731468

Reaction notes

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