Sodium borohydride → HCID 22418825, compound

HRID 893111Notes

Reaction equation

HRID 893111 reaction equation
[CH2:1]1[CH2:22][O:21][C:20]2[C:3](=[C:4]([CH:17]=[CH:18][CH:19]=2)[CH2:5][CH:6]([C:14]([O-])=[O:15])[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[O:2]1.[BH4-].[Na+]>C(O)C.C(OCC)(=O)C>[CH2:1]1[CH2:22][O:21][C:20]2[C:3](=[C:4]([CH:17]=[CH:18][CH:19]=2)[CH2:5][CH:6]([CH2:14][OH:15])[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[O:2]1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 86745926HCID 86745926, compound

Product 1

HCID 22418825HCID 22418825, compoundYield 36%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

761 mg of tert-butyl (2,3-ethylenedioxybenzyl)malonate was dissolved in 20 ml of ethanol. Then, 0.57 g of sodium borohydride was added thereto, and the mixture was stirred at room temperature overnight. The reaction solution was diluted with 150 ml of ethyl acetate and washed with 100 ml of water and then with 100 ml of a saturated sodium chloride aqueous solution. The organic layer was dried over anhydrous magnesium sulfate, then concentrated under reduced pressure and purified by silica gel column chromatography (n-hexane/ethyl acetate=3/1) to obtain 241 mg (yield: 36%) of the desired product as syrup.

Workup

  1. washwashed with 100 ml of water
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. custompurified by silica gel column chromatography (n-hexane/ethyl acetate=3/1)

Sources & evidence

ORD record
ord-8e42af29f2f6446ca127e428bdb0a866
Source dataset
uspto-grants-1992_06
Patent number
US05122523

Reaction notes

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