HCID 3035611, compound → HCID 86752787, compound

HRID 964361Notes

Reaction equation

HRID 964361 reaction equation
[OH:1][CH:2](C(O)C)[CH:3]=[CH:4][C:5]([O:7][CH:8]1[CH2:15][CH2:14][C:11]2([O:13][CH2:12]2)[CH:10]([C:16]2([CH3:24])[CH:18]([CH2:19][CH:20]=[C:21]([CH3:23])[CH3:22])[O:17]2)[CH:9]1[O:25][CH3:26])=[O:6].I([O-])(=O)(=O)=O.[Na+]>CO.O.C(OCC)C>[CH:2]([CH:3]=[CH:4][C:5]([O:7][CH:8]1[CH2:15][CH2:14][C:11]2([O:13][CH2:12]2)[CH:10]([C:16]2([CH3:24])[CH:18]([CH2:19][CH:20]=[C:21]([CH3:23])[CH3:22])[O:17]2)[CH:9]1[O:25][CH3:26])=[O:6])=[O:1]

Participants

6

Reactant 2

HCID 3035611HCID 3035611, compoundHCID 23667635Sodium periodate

Product 1

HCID 86752787HCID 86752787, compoundYield 68.6%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of 6-(4,5-dihydroxy-2-hexenoyloxy)-5-methoxy-4-(2-methyl-3-(3-methyl-2-butenyl)oxiranyl]-1-oxaspiro[2,5]octane (412 mg) in a mixture of methanol (4 ml) and water (4 ml) was added sodium periodate (215 mg) in several portions at 5° C. The mixture was stirred for half hour at the same temperature and diluted with diethyl ether (30 ml). The mixture was washed with brine, dried, and concentrated in vacuo to give a crude oil, which was purified by column chromatography on silica gel (elution by diethyl etherln-hexane =1/1) to yield 6-(3-formylacryloyloxy)-5-methoxy-4-(2-methyl-3-(3-methyl-2-butenyl)oxiranyl]-1-oxaspiro[2,5]octane (251 mg) as an oil.

Workup

  1. washThe mixture was washed with brine
  2. customdried
  3. concentrationconcentrated in vacuo
  4. customto give a crude oil, which
  5. customwas purified by column chromatography on silica gel (elution by diethyl etherln-hexane =1/1)

Sources & evidence

ORD record
ord-b3abae4520474f909cdebb0e48235805
Source dataset
uspto-grants-1998_06
Patent number
US05767293

Reaction notes

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