Sodium borohydride → HCID 22914122, compound

HRID 1721266Notes

Reaction equation

HRID 1721266 reaction equation
[BH4-].[Na+].[CH3:3][C:4]1([CH3:17])[C:8]([CH3:9])=[CH:7][CH2:6][CH:5]1[CH:10]([CH2:13][C:14]([CH3:16])=[CH2:15])[CH:11]=[O:12]>C(O)C>[CH3:3][C:4]1([CH3:17])[C:8]([CH3:9])=[CH:7][CH2:6][CH:5]1[CH:10]([CH2:13][C:14]([CH3:16])=[CH2:15])[CH2:11][OH:12]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 22914111HCID 22914111, compound

Product 1

HCID 22914122HCID 22914122, compoundYield 63.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
0 °C

Procedure

A 500 ml 3 neck flask was charged with 250 ml of ethanol and 6.0 g of sodium borohydride (0.16 mole). To the flask maintained at 0° C. in an ice bath was added dropwise 74.6 g of the aldehyde from example 1 at a purity of 84.3% (0.30 mole) in 100 ml of ethanol. The batch was stirred 45 minutes at 0° C. The reaction was now quenched by the addition of 50 ml of 25% hydrochloric acid at 0°-5° C. The mixture was poured onto 300 ml of brine and extracted with 3×100 ml of hexane. The hexane was washed with 2×250 ml of brine, dried with magnesium sulfate, filtered, and concentrated in vacuo. The batch was distilled through a 10 cm vigreaux column to afford 48 g of purified product (58% yield). BP 78° C./0.25 mmHg; 1H-NMR (300 MHz), δ0.91 (3H, s), 1.09 (3H, s), 1.60 (3H, s), 1.77 (3H, s), 1.85-2.30 (7H, m), 3.66 (2H, m), 4.80 (2H, s), 5.24 (1H, s); 13C-NMR (75 MHz), δ12.90, 20.20, 22.76, 27.36, 34.07, 39.57, 40.61, 47.53, 50.32, 64.52, 112.63, 122.26, 146.38, 149.32; IR (Neat), 3370, 2960, 2940, 1650, 1040 cm-1 ; MS (m/e), 208 (M+), 95 (Base).

Workup

  1. customThe reaction was now quenched by the addition of 50 ml of 25% hydrochloric acid at 0°-5° C
  2. additionThe mixture was poured onto 300 ml of brine
  3. extractionextracted with 3×100 ml of hexane
  4. washThe hexane was washed with 2×250 ml of brine
  5. dry with materialdried with magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. distillationThe batch was distilled through a 10 cm vigreaux column

Sources & evidence

ORD record
ord-01b8fd78821f4c98902e87aa3c7fb2b4
Source dataset
uspto-grants-1996_04
Patent number
US05510326

Reaction notes

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