Toluene → HCID 19010982, compound

HRID 1741962Notes

Reaction equation

HRID 1741962 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.C1(C)C=CC=CC=1.[CH3:18][C:19]1([CH3:37])[O:36][CH:22]2[CH:23]3[CH2:28][O:27][C:26](=[O:29])[CH:25]=[C:24]3[CH2:30][CH:31]([O:32][CH2:33][O:34][CH3:35])[CH:21]2[O:20]1.S([O-])([O-])(=O)=O.[Na+].[Na+]>C(OCC)C.C(OCC)(=O)C>[CH3:18][C:19]1([CH3:37])[O:36][CH:22]2[CH:23]3[CH2:28][O:27][CH:26]([OH:29])[CH:25]=[C:24]3[CH2:30][CH:31]([O:32][CH2:33][O:34][CH3:35])[CH:21]2[O:20]1

Participants

7

Reactant 4

HCID 1140TolueneHCID 24436Sodium SulfateHCID 19010990HCID 19010990, compoundHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 19010982HCID 19010982, compoundYield 179.7%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Procedure

Under an argon atmosphere, 18 microliters of diisobutyl aluminum hydride (0.5N toluene solution) was added at -78° C. to a 0.5 ml toluene solution of 2.1 mg 1,5,6,7,8,8a-hexahydro-7,8-(dimethylmethylenedioxy)-6-methoxymethoxy-3H-2-benzopyran-3-one, and stirring was conducted for 2 hours. After the temperature was elevated to 0° C., the reaction mixture was diluted with diethyl ether, and a saturated sodium sulfate aqueous solution was added until a white precipitate was formed. To the obtained reaction mixture was added ethyl acetate, and the organic layer was washed with a saturated sodium chloride aqueous solution and dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to afford 3.8 mg of 1,5,6,7,8,8a-hexahydro-7,8-(dimethylmethylenedioxy)-6-methoxymethoxy-3H-2-benzopyran-3-ol having the following properties (yield 100%).

Workup

  1. customwas elevated to 0° C.
  2. customwas formed
  3. customTo the obtained reaction mixture
  4. washthe organic layer was washed with a saturated sodium chloride aqueous solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-8ae29f5fbdfc4c7684d524a8cc6c0219
Source dataset
uspto-grants-1994_08
Patent number
US05334740

Reaction notes

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