Methyl iodide → HCID 131719265, compound

HRID 1781532Notes

Reaction equation

HRID 1781532 reaction equation
[Si:1]([O:8][C:9]1[C:17]([CH2:18]/[CH:19]=[C:20](\[CH3:29])/[CH:21]([OH:28])[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])=[C:16]([O:30][CH3:31])[C:15]([CH3:32])=[C:14]2[C:10]=1[C:11](=[O:33])[O:12][CH2:13]2)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH3:34]I>CC#N.[Ag]=O>[Si:1]([O:8][C:9]1[C:17]([CH2:18]/[CH:19]=[C:20](\[CH3:29])/[CH:21]([O:28][CH3:34])[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])=[C:16]([O:30][CH3:31])[C:15]([CH3:32])=[C:14]2[C:10]=1[C:11](=[O:33])[O:12][CH2:13]2)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 6328Methyl iodideHCID 131719266HCID 131719266, compound

Product 1

HCID 131719265HCID 131719265, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 92152Silver(II) oxideCatalystHCID 6342AcetonitrileSolvent

Procedure

Ethyl (E)-6-(1,3-dihydro-4-tert -butyldimethylsilyloxy-6-methoxy -7-methyl-3-oxoisobenzofuran-5-yl)-3-hydroxy-4-methyl-4-hexenoate (974 mg) was dissolved in a 6:1 mixture of methyl iodide in CH3CN (25 ml). Silver oxide was then added (5.1 g) and the mixture heated at reflux for 24 hr. The mixture was cooled to room temperature and filtered through a bed of celite. The celite was washed with CH2Cl2 (80 ml) and ethyl acetate (80 ml). The combined organic layers were evaporated to dryness and the residue passed through a flash column (silica gel, hexanes-EtOAc 8:2) to afford 601 mg (60%) of ethyl (E)-6-(1,3-dihydro-4-tert-butyldimethylsilyloxy-6-methoxy-7-methyl-3-oxoisobenzofuran-5-yl) -3-methoxy-4-methyl-4-hexenoate the product as a colorless oil.

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 24 hr
  3. filtrationfiltered through a bed of celite
  4. washThe celite was washed with CH2Cl2 (80 ml) and ethyl acetate (80 ml)
  5. customThe combined organic layers were evaporated to dryness

Sources & evidence

ORD record
ord-80a07f86bd5b4e04b69809945bd1ada7
Source dataset
uspto-grants-1997_05
Patent number
US05633279

Reaction notes

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