Sodium borohydride → HCID 178448091, compound

HRID 1941718Notes

Reaction equation

HRID 1941718 reaction equation
C([O:3][C:4](=O)[CH2:5][C:6](=[O:16])[C@H:7]1[CH2:12][CH2:11][C@H:10]([CH2:13][CH2:14][CH3:15])[CH2:9][CH2:8]1)C.[BH4-].[Na+]>C(O)C>[CH2:13]([C@H:10]1[CH2:11][CH2:12][C@H:7]([CH:6]([OH:16])[CH2:5][CH2:4][OH:3])[CH2:8][CH2:9]1)[CH2:14][CH3:15]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 178448092HCID 178448092, compound

Product 1

HCID 178448091HCID 178448091, compoundYield 73.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

An ethanol (300 ml) solution of (3-oxo-3-(trans-4-propyl-cyclohexyl)-propionic acid ethyl ester (3) (220.0 g) prepared in the second step was added dropwise at 50° C. or lower to a suspension of sodium borohydride (45 g) in ethanol (500 ml), in a reaction vessel under an atmosphere of nitrogen, and the stirring was continued at room temperature for 5 hours. The reaction mixture was quenched with water (1,000 ml), to which ethyl acetate (500 ml) was added to give two layers The water layer was extracted with ethyl acetate (500 ml) twice, and the combined organic layer was washed with water and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography (silica gel: 500 g, eluent: heptane/ethyl acetate=50/50 by volume) to give 1-(trans-4-propyl-cyclohexyl)-propane-1,3-diol (4) (135 g) in 67% yield.

Workup

  1. customThe reaction mixture was quenched with water (1,000 ml), to which ethyl acetate (500 ml)
  2. additionwas added
  3. customto give two layers The water layer
  4. extractionwas extracted with ethyl acetate (500 ml) twice
  5. washthe combined organic layer was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationThe solvent was distilled off under reduced pressure
  8. customThe residue was purified by silica gel chromatography (silica gel: 500 g, eluent: heptane/ethyl acetate=50/50 by volume)

Sources & evidence

ORD record
ord-71b8de1d498949118ed3369b163e96ba
Source dataset
uspto-grants-2013_03
Patent number
US08389073B2

Reaction notes

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