Sodium borohydride → 2-[2-(Propan-2-yl)-1,3-dioxolan-2-yl]ethan-1-ol

HRID 2037491Notes

Reaction equation

HRID 2037491 reaction equation
C([O:3][C:4](=O)[CH2:5][C:6]1([CH:11]([CH3:13])[CH3:12])[O:10][CH2:9][CH2:8][O:7]1)C.[BH4-].[Na+]>CO.[Cl-].[Cl-].[Zn+2]>[CH:11]([C:6]1([CH2:5][CH2:4][OH:3])[O:10][CH2:9][CH2:8][O:7]1)([CH3:13])[CH3:12]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 10560027HCID 10560027, compound

Product 1

HCID 141623372-[2-(Propan-2-yl)-1,3-dioxolan-2-yl]ethan-1-olYield 45.7%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 887MethanolSolvent

Procedure

To a solution of (2-isopropyl-[1,3]dioxolan-2-yl)-acetic acid ethyl ester (83 g, 0.41 mol) in MeOH (1600 mL) was added NaBH4 (78 g, 2.05 mol) and ZnCl2 (8.3 g). The mixture was stirred overnight. The mixture was concentrated, and the residue was dissolved in the mixture of EtOAc and water. The layers were separated, and the aqueous layer was extracted with EtOAc. The combined organic phase was dried over Na2SO4, and concentrated to give the crude product, which was purified by column to give 2-(2-isopropyl-[1,3]dioxolan-2-yl)-ethanol (30 g, crude).

Workup

  1. concentrationThe mixture was concentrated
  2. dissolutionthe residue was dissolved in the mixture of EtOAc and water
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with EtOAc
  5. dry with materialThe combined organic phase was dried over Na2SO4
  6. concentrationconcentrated
  7. customto give the crude product, which
  8. customwas purified by column

Sources & evidence

ORD record
ord-1f8d08b416c147b289865c0624600335
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

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