Sodium borohydride → HCID 19046297, compound

HRID 1781557Notes

Reaction equation

HRID 1781557 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].[BH4-].[Na+]>O1CCCC1.CO.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 3

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

Product 1

HCID 19046297HCID 19046297, compoundYield 51.5%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 21899815MeOH tetrahydrofuranSolvent

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 tetrahydrofuran/methanol (12 mL, 4/1) was treated 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-a6c7fd2f95eb41c2a437b2e2f311beb5
Source dataset
uspto-grants-1997_05
Patent number
US05633279

Reaction notes

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