Ethyl vinyl ether → HCID 19046364, compound

HRID 2396645Notes

Reaction equation

HRID 2396645 reaction equation
[CH3:1][O:2][C:3]1[C:11]([CH3:12])=[C:10]2[C:6]([C:7](=[O:13])[O:8][CH2:9]2)=[C:5]([O:14][S:15]([C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=2)(=[O:17])=[O:16])[C:4]=1[CH2:25][C:26]1[CH2:30][CH2:29][CH:28](OC=C)[C:27]=1[CH3:34].Cl([O-])(=O)(=O)=O.[Li+].[CH:41]([O:43]CC)=[CH2:42]>CCOCC.C(=O)(O)[O-].[Na+]>[CH3:1][O:2][C:3]1[C:11]([CH3:12])=[C:10]2[C:6]([C:7](=[O:13])[O:8][CH2:9]2)=[C:5]([O:14][S:15]([C:18]2[CH:19]=[CH:20][C:21]([CH3:24])=[CH:22][CH:23]=2)(=[O:17])=[O:16])[C:4]=1[CH2:25][C:26]1[CH2:30][CH2:29][CH:28]([CH2:42][CH:41]=[O:43])[C:27]=1[CH3:34]

Participants

6

Reactant 3

HCID 8023Ethyl vinyl etherHCID 19046422HCID 19046422, compoundHCID 23665649Lithium perchlorate

Product 1

HCID 19046364HCID 19046364, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of 3-(1,3-dihydro-6-methoxy-7-methyl-3-oxo-4-p-toluenesulfonyloxy-5-isobenzofurnylmethyl)-2-methylcyclopent-2-en-1-ol (0.157 g) in ethyl vinyl ether (10 mL) was added mercuric acetate (0.052 g). After stirring for 30 hours at ambient temperature, the reaction was diluted with ether and passed quickly through a fritted funnel half filled with celite and capped with silica. To this ethereal solution [containing 3-(1,3-dihydro-6-methoxy-7-methyl-3-oxo-4-p-toluenesulfonyloxy-5-isobenzofuranylmethyl)-2-methyl-1-vinyloxycyclopent-2-ene, which was not isolated or characterized] was then added lithium perchlorate (10 mL, 0.5M solution in ether). After 0.5 hours, the reaction was diluted with aqueous sodium bicarbonate and washed with brine. Drying over magnesium sulfate was followed by filtration and solvent removal. The product 3-(1,3-dihydro-6-methoxy-7-methyl-3-oxo-4-p-toluenesulfonyloxy-5-isobenzofuranylmethyl)-2-methylcyclopent-2-en-1-ylacetaldehyde (0.050 g) was finally obtained after chromatography (hexanes/ethyl acetate, 2/1).

Workup

  1. custompassed quickly through a fritted funnel
  2. additionhalf filled with celite
  3. customcapped with silica
  4. customwas not isolated
  5. waitAfter 0.5 hours
  6. washwashed with brine
  7. dry with materialDrying over magnesium sulfate
  8. filtrationwas followed by filtration and solvent removal

Sources & evidence

ORD record
ord-6c58e5ea89a04c5f8479bd2bf2f5aa95
Source dataset
uspto-grants-1996_02
Patent number
US05493030

Reaction notes

Loading…