Sodium borohydride → HCID 67083828, compound

HRID 2066023Notes

Reaction equation

HRID 2066023 reaction equation
[O:1]1[CH2:5][CH2:4][CH2:3][C@@H:2]1[C:6](=[O:9])[CH2:7][CH3:8].[BH4-].[Na+]>CO>[O:1]1[CH2:5][CH2:4][CH2:3][CH:2]1[C@H:6]([OH:9])[CH2:7][CH3:8]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 670838321-[(2R)-Tetrahydro-2-furanyl]-1-propanone

Product 1

HCID 67083828HCID 67083828, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a cooled (0° C.) solution of (R)-1-(tetrahydrofuran-2-yl)propan-1-one (16.16 g, 1 equiv) in MeOH was added portionwise sodium tetrahydroborate (4.77 g, 1 equiv). After stirring at 0° C. for 1 hour, the reaction was quenched with 5M HCl and allowed to stir for further for 10 minutes. The mixture was concentrated in vacuo to remove MeOH and EtOAc and water were added. The organic portion was separated and the aqueous layer extracted several times with EtOAc. The combined organic extracts were dried (MgSO4) and concentrated in vacuo to afford the title compound.

Workup

  1. customthe reaction was quenched with 5M HCl
  2. stirringto stir for further for 10 minutes
  3. concentrationThe mixture was concentrated in vacuo
  4. customto remove MeOH and EtOAc and water
  5. additionwere added
  6. customThe organic portion was separated
  7. extractionthe aqueous layer extracted several times with EtOAc
  8. dry with materialThe combined organic extracts were dried (MgSO4)
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a6a32943da674aa28645d23bf78d947a
Source dataset
uspto-grants-2012_10
Patent number
US08288588B2

Reaction notes

Loading…