HCID 57112010, compound → HCID 54317759, compound

HRID 1781554Notes

Reaction equation

HRID 1781554 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][CH:26]=[C:27]([CH3:30])[CH:28]=[O:29].[CH:31]([Mg]Br)=[CH2:32]>O1CCCC1.C(OCC)(=O)C>[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][CH:26]=[C:27]([CH3:30])[CH:28]([OH:29])[CH:31]=[CH2:32]

Participants

5

Reactant 2

HCID 57112010HCID 57112010, compoundHCID 178418507HCID 178418507, compound

Product 1

HCID 54317759HCID 54317759, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-(1,3-dihydro-6-methoxy-7-methyl-3-oxo-4-p-toluenesulfonyloxy-5-isobenzofuranyl)2-methylbut-2-enaldehyde (0.90 g) in tetrahydrofuran (40 mL) was added vinylmagnesium bromide (4.5 mL of a 1M solution in tetrahydrofuran). After stirring for 0.5 hours, the reaction was diluted with ethyl acetate and washed successively with aqueous ammonium chloride and brine. Drying over magnesium sulfate was followed by filtration and solvent removal to leave a residual oil, 6-(1,3-dihydro -6-methoxy-7-methyl-3-oxo-4-p-toluenesulfonyloxy-5-isobenzofuranyl)-3-hydroxy-4-methylhexa-1,4-diene, which was carried on without further purification.

Workup

  1. washwashed successively with aqueous ammonium chloride and brine
  2. dry with materialDrying over magnesium sulfate
  3. filtrationwas followed by filtration and solvent removal

Sources & evidence

ORD record
ord-cf23d575e9194b7e8f2f8af78c19eb28
Source dataset
uspto-grants-1997_05
Patent number
US05633279

Reaction notes

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