Dichloromethane → HCID 86758089, compound

HRID 1937123Notes

Reaction equation

HRID 1937123 reaction equation
[CH3:1][C@@H:2]1[O:6][C:5](=[O:7])[CH:4]=[CH:3]1.[CH:8]1[O:9][CH:10]=[C:11]2[C:16]=1[CH2:15][CH2:14][CH2:13][CH2:12]2.C(Cl)Cl>CCOCC.Cl([O-])(=O)(=O)=O.[Li+]>[O:9]1[C@@H:10]2[C@H:4]3[C@H:3]([C@H:8]1[C:16]1[CH2:15][CH2:14][CH2:13][CH2:12][C:11]=12)[C@H:2]([CH3:1])[O:6][C:5]3=[O:7]

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 954874092694-51-4HCID 109424064,5,6,7-tetrahydroisobenzofuran

Product 1

HCID 86758089HCID 86758089, compoundYield 58.2%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 23665649Lithium perchlorateSolvent

Procedure

To 224.0 mg(2.28 mmol) of (S)-5-methyl-2(5H)-furanone were added 557.9 mg(1.5 equivalents) of 4,5,6,7-tetrahydroisobenzofuran in 2 ml of dehydrated ether solution and 1.06 g of lithium perchlorate, and, after flushing with argon, the mixture was stirred for 168 hours at room temperature. The reaction mixture was poured into 20 ml of water, which was extracted with methylene chloride(10 ml×3). The organic layer was dried over anhydrous magnesium sulfate, filtered and solvent was distilled off under reduced pressure. The residue was purified by means of silica gel column chromatography(methylene chloride, then methylene chloride:ethyl acetete=10:1) to obtain 292.2 mg of (3S, 3aS, 4S, 9R, 9aR)-4,9-epoxy-3-methyl-3a,4,5,6,7,8,9,9a-octahydronaphtho[2,3-c]furan-1(3H)-one (yield 58%).

Workup

  1. customafter flushing with argon
  2. additionThe reaction mixture was poured into 20 ml of water, which
  3. extractionwas extracted with methylene chloride(10 ml×3)
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. distillationsolvent was distilled off under reduced pressure
  7. customThe residue was purified by means of silica gel column chromatography(methylene chloride

Sources & evidence

ORD record
ord-12c40f14b8c84c1e88f87f88416d6c00
Source dataset
uspto-grants-2002_05
Patent number
US06392059B1

Reaction notes

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