Methanol → HCID 19046297, compound

HRID 2396644Notes

Reaction equation

HRID 2396644 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][C:28](=[O:31])[C:27]=1[CH3:32].O.O.O.O.O.O.O.[Cl-].[Cl-].[Cl-].[Ce+3].CO.[BH4-].[Na+]>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][C:26]1[CH2:30][CH2:29][CH:28]([OH:31])[C:27]=1[CH3:32]

Participants

6

Reactant 4

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 19046376HCID 19046376, compoundHCID 21585214Cerium trichloride heptahydrate

Product 1

HCID 19046297HCID 19046297, compoundYield 51.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-(1,3-dihydro-6-methoxy-7-methyl-3-oxo-4-p-toluenesulfonyloxy-5-isobenzofuranylmethyl)-2-methylcyclopent-2-en-1-one (0.17 g) and cerium trichloride heptahydrate (0.172 g) in tetrahydrofurn/methanol (12 mL, 4/1) was trea=ed with sodium borohydride (0.035 g). After 0.5 hours, the reaction was diluted with ethyl acetate and washed with brine. Drying over magnesium sulfate was followed by filtration and solvent removal. Chromatography (hexanes/methylene chloride/ether, 1/1/1) gave the product 3-(1,3-dihydro-6-methoxy-7-methyl-3-oxo-4-p-toluenesulfonyloxy-5-isobenzofuranylmethyl)-2-methylcyclopent-2-en-1-ol (0.088 g) as a solid m.p. 108.0°-111.5° C.

Workup

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

Sources & evidence

ORD record
ord-7f4b6b8fc67b4e16939d661dc68961e7
Source dataset
uspto-grants-1996_02
Patent number
US05493030

Reaction notes

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