Sodium borohydride → HCID 90134892, compound

HRID 1483041Notes

Reaction equation

HRID 1483041 reaction equation
[CH:1]1([C:4](=[O:15])[CH2:5][O:6][CH2:7][CH:8]2[CH2:12][O:11][C:10]([CH3:14])([CH3:13])[O:9]2)[CH2:3][CH2:2]1.[BH4-].[Na+]>CO>[CH:1]1([CH:4]([OH:15])[CH2:5][O:6][CH2:7][CH:8]2[CH2:12][O:11][C:10]([CH3:13])([CH3:14])[O:9]2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 90135527HCID 90135527, compound

Product 1

HCID 90134892HCID 90134892, compoundYield 99.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Dissolve 1-cyclopropyl-2-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)ethanone (1.2 g, 5.6 mmol), MeOH (20 mL) and sodium tetrahydroborate (310 mg, 8.19 mmol). Stir at ambient temperature for 1 hour. Concentrate under reduced pressure. Add water (30 mL) and extract with EtOAc (3×). Combine the extracts; wash with brine; and dry over MgSO4. Filter; collect the filtrate; and remove the solvents under reduced pressure to give the title compound as a colorless oil (1.2 g, 99%). MS (m/z): 199 (M-H2O+1).

Workup

  1. concentrationConcentrate under reduced pressure
  2. extractionAdd water (30 mL) and extract with EtOAc (3×)
  3. washwash with brine
  4. dry with materialand dry over MgSO4
  5. filtrationFilter
  6. customcollect the filtrate
  7. customand remove the solvents under reduced pressure

Sources & evidence

ORD record
ord-fd5cecbe1c7442c0872baecb229e3681
Source dataset
uspto-grants-2016_08
Patent number
US09416138B2

Reaction notes

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