Sodium borohydride → HCID 71093329, compound

HRID 332666Notes

Reaction equation

HRID 332666 reaction equation
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][CH:17]=1)[CH:13]=[O:14].[BH4-].[Na+]>C(O)C>[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:11]=[C:12]([CH2:13][OH:14])[CH:15]=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86676901HCID 86676901, compound

Product 1

HCID 71093329HCID 71093329, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To an ice-cooled solution of 3-(3-(1,3-dioxolan-2-yl)propoxy)benzaldehyde (prepared as in Example 10; Step 1) (3.08 g, 13.1 mmol) in ethanol (66 mL), was added sodium borohydride (1.98 g, 52.4 mmol). The reaction mixture was allowed to warm to ambient temperature and stirred at ambient temperature for 16 hours. The reaction mixture was carefully quenched with saturated aqueous ammonium chloride and extracted twice with DCM. The combined organic phases were poured through a hydrophobic column, and the solvent was evaporated at reduced pressure to afford the title compound as a colourless oil (2.96 g, 95%).

Workup

  1. customThe reaction mixture was carefully quenched with saturated aqueous ammonium chloride
  2. extractionextracted twice with DCM
  3. additionThe combined organic phases were poured through a hydrophobic column
  4. customthe solvent was evaporated at reduced pressure

Sources & evidence

ORD record
ord-4542960545264245a2d2563c0e8056c6
Source dataset
uspto-grants-2014_11
Patent number
US08877774B2

Reaction notes

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