Methyl chloroformate → HCID 14302871, compound

HRID 654849Notes

Reaction equation

HRID 654849 reaction equation
[CH3:1][O:2][C:3]1[C:12]([O:13][CH3:14])=[C:11]([OH:15])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]=1[OH:16].Cl[C:18]([O:20][CH3:21])=[O:19].C(N(CC)CC)C>O1CCCC1>[CH3:14][O:13][C:12]1[C:3]([O:2][CH3:1])=[C:4]([O:16][C:18]([O:20][CH3:21])=[O:19])[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:11]=1[O:15][C:18]([O:20][CH3:21])=[O:19]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 14302861HCID 14302861, compound

Product 1

HCID 14302871HCID 14302871, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1.0 g of 2,3-dimethoxy-1,4-dihydroxynaphthalene, prepared as shown in Preparation 5, in 50 ml of tetrahydrofuran was added 1.40 g of methyl chloroformate followed by 1.50 g of triethylamine. The mixture was stirred at room temperature for 16 hours, filtered, then the solvent removed under reduced pressure. The residue was dissolved in diethyl ether, washed with dilute hydrochloric acid and dried over anhydrous sodium sulfate. The ether was removed under reduced pressure and the residue chromatographed on silica gel, eluting with a 1:1 mixture of methylene chloride and hexane, to give 2,3-dimethoxy-1,4-di(methoxycarbonyloxy)naphthalene, m.p. 53°-54° C.

Workup

  1. filtrationfiltered
  2. customthe solvent removed under reduced pressure
  3. dissolutionThe residue was dissolved in diethyl ether
  4. washwashed with dilute hydrochloric acid
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe ether was removed under reduced pressure
  7. customthe residue chromatographed on silica gel
  8. washeluting with a 1:1 mixture of methylene chloride and hexane

Sources & evidence

ORD record
ord-5b81b3e1e88e4fd4b974b204fae6cfab
Source dataset
uspto-grants-1992_07
Patent number
US05134161

Reaction notes

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