Sodium borohydride → HCID 16738000, compound

HRID 899572Notes

Reaction equation

HRID 899572 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, 1H), 8.17 (d, J=8.3 Hz, 1H), 7.61 (m, 1H), 7.53 (m, 1H), 7.41 (d, J=7.8 Hz, 1H), 7.35 (t, J=7.8 Hz, 2H), 7.13 (t, J=7.3 Hz, 1H), 7.05 (dd, J=8.6, 1.2 Hz, 2H), 6.88 (d, J=7.8 Hz, 1H), 5.12 (s, 2H).

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-eb146e2d79494277aeb1f200d13a9674
Source dataset
uspto-grants-2008_04
Patent number
US07355079B2

Reaction notes

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