Sodium borohydride → HCID 85877287, compound

HRID 2176244Notes

Reaction equation

HRID 2176244 reaction equation
[C:1]([C:4]1([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:9][O:8][CH2:7][O:6][CH2:5]1)(=[O:3])[CH3:2].[BH4-].[Na+]>C(O)C>[OH:3][CH:1]([C:4]1([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:9][O:8][CH2:7][O:6][CH2:5]1)[CH3:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86706083HCID 86706083, compound

Product 1

HCID 85877287HCID 85877287, compoundYield 84.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 5-acetyl-1,3-dioxane-5-carboxylate (2) (22.3 g, 0.11 mol) was dissolved in ethanol (100 mL) and sodium borohydride (2.08 g, 0.055 mol) was added at 0° C. in portions. The mixture was stirred at the same temperature for 1 h. The excess of sodium borohydride was destroyed with acetone and the solution was extracted with ethyl acetate (3×600 mL). The combined organic extracts were concentrated in vacuo to give the title compound (18.9 g, 84%) as colorless oil.

Workup

  1. customThe excess of sodium borohydride was destroyed with acetone
  2. extractionthe solution was extracted with ethyl acetate (3×600 mL)
  3. concentrationThe combined organic extracts were concentrated in vacuo

Sources & evidence

ORD record
ord-02d4ad1173de45eb84d325529e9fa9e2
Source dataset
uspto-grants-2015_06
Patent number
US09062092B2

Reaction notes

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