Sodium borohydride → HCID 16738000, compound

HRID 2252396Notes

Reaction equation

HRID 2252396 reaction equation
[O:1]([C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([CH:18]=[O:19])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>C(O)C>[O:1]([C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([CH2:18][OH:19])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 108244354-phenoxynaphthaldehyde

Product 1

HCID 16738000HCID 16738000, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 134 (0.28 g, 1.12 mmol) in ethanol (20 mL) was added sodium borohydride (0.042 g, 1.12 mmol). After stirring at room temperature for 15 min, the reaction was quenched with water and extracted with ethyl ether. The organic layer was washed with brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure to give the crude product. The crude mixture was purified via flash SiO2 chromatography (ethyl acetate/hexanes (25%/75%) to give 135 (0.28 g, 95% yield): 1H-NMR (400 MHz, chloroform-d) δ 8.29 (d, J=8.3 Hz, 1 H), 8.17 (d, J=8.3 Hz, 1 H), 7.61 (m, 1 H), 7.53 (m, 1 H), 7.41 (d, J=7.8 Hz, 1 H), 7.35 (t, J=7.8 Hz, 2 H), 7.13 (t, J=7.3 Hz, 1 H), 7.05 (dd, J=8.6, 1.2 Hz, 2 H), 6.88 (d, J=7.8 Hz, 1 H), 5.12 (s, 2 H).

Workup

  1. customthe reaction was quenched with water
  2. extractionextracted with ethyl ether
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto give the crude product
  8. customThe crude mixture was purified via flash SiO2 chromatography (ethyl acetate/hexanes (25%/75%)

Sources & evidence

ORD record
ord-ac1b497037114599967e46e9f675eebd
Source dataset
uspto-grants-2008_01
Patent number
US07321065B2

Reaction notes

Loading…