HCID 57112010, compound → HCID 54317759, compound

HRID 2396642Notes

Reaction equation

HRID 2396642 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 nd 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-8da8b75a86154f63b8cf7dcce34277b6
Source dataset
uspto-grants-1996_02
Patent number
US05493030

Reaction notes

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