Methyl chloroformate → 4,5-Bis(methoxycarbonyloxy)-9,10-dihydro-9,10-dioxo-2-anthracenecarboxylic acid butyl ester

HRID 2379454Notes

Reaction equation

HRID 2379454 reaction equation
[CH2:1]([O:5][C:6]([C:8]1[CH:21]=[C:20]([OH:22])[C:19]2[C:18](=[O:23])[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][C:16]=3[OH:24])[C:11](=[O:25])[C:10]=2[CH:9]=1)=[O:7])[CH2:2][CH2:3][CH3:4].C(N(CC)CC)C.Cl[C:34]([O:36][CH3:37])=[O:35]>O1CCCC1>[CH2:1]([O:5][C:6]([C:8]1[CH:21]=[C:20]([O:22][C:34]([O:36][CH3:37])=[O:35])[C:19]2[C:18](=[O:23])[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][C:16]=3[O:24][C:6]([O:5][CH3:1])=[O:7])[C:11](=[O:25])[C:10]=2[CH:9]=1)=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 54443434HCID 54443434, compound

Product 1

HCID 539595674,5-Bis(methoxycarbonyloxy)-9,10-dihydro-9,10-dioxo-2-anthracenecarboxylic acid butyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2.7 g (8 mmoles) of the product of Example 15 are dissolved in 100 ml of anhydrous tetrahydrofuran; the resulting solution is added first with 2.42 g (24 mmoles) of anhydrous triethylamine, then, after cooling to 0°-5° C., with 1.6 g (17 mmoles) of methyl chloroformate. The reaction is complete within 3 hours, keeping room temperature. After that, solvent is evaporated off under reduced pressure and the residue is washed with acidulated water, the product is filtered, washed and crystallized from ethyl ether. M.p. 200°-202° C.

Workup

  1. customkeeping room temperature
  2. customAfter that, solvent is evaporated off under reduced pressure
  3. washthe residue is washed with acidulated water
  4. filtrationthe product is filtered
  5. washwashed
  6. customcrystallized from ethyl ether

Sources & evidence

ORD record
ord-6d69df4340aa4cb18c0a07cb697980be
Source dataset
uspto-grants-1994_11
Patent number
US05362750

Reaction notes

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