Sodium borohydride → HCID 57812760, compound

HRID 912034Notes

Reaction equation

HRID 912034 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][CH2:6][C:7]2=[O:12].[BH4-].[Na+]>CO>[F:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][CH2:6][CH:7]2[OH:12]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 154910385-Fluoro-1,2,3,4-tetrahydronaphthalen-1-one

Product 1

HCID 57812760HCID 57812760, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of 5-fluoro-3,4-dihydronaphthalen-1(2H)-one (1.26 mmol) in MeOH (4 mL) at 0° C. was quickly charged with a solution of sodium borohydride (3.23 mmol, 2.5 eq) in MeOH (2 mL). The reaction was stirred for 1.5 h from 0° C. to ambient temperature. The reaction was quenched with water and extracted with ether. All organic layers were combined and dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. The crude was dissolved in minimal CH2Cl2 and was purified by chromatography on silica gel [0.5″×10″ glass column, eluting with neat CH2Cl2→5:1 CH2Cl2:EtOAc]. Fractions containing product were combined and concentrated in vacuo, giving the title material as a light yellow oil. 1H NMR (400 MHz, CDCl3) δ=1.73 (d, J=6.8 Hz, 1H), 1.75-1.90 (m, 2H), 1.91-2.10 (m, 2H), 2.61-2.86 (m, 2H), 4.67-4.83 (m, 1H), 6.90 (ddd, J=8.5, 8.5, 2.8 Hz, 1H), 7.06 (dd, J=8.5, 5.7 Hz, 1H), 7.17 (dd, J=9.6, 2.8 Hz, 1H). MS (ES+): m/z 149.02 (100) [MH+−OH]. HPLC: tR=2.96 min (ZQ3, polar—5 min).

Workup

  1. customThe reaction was quenched with water
  2. extractionextracted with ether
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. dissolutionThe crude was dissolved in minimal CH2Cl2
  7. customwas purified by chromatography on silica gel [0.5″×10″ glass column
  8. washeluting with neat CH2Cl2→5:1 CH2Cl2
  9. additionFractions containing product
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5acb86ec58e148cc8574c73462173041
Source dataset
uspto-grants-2011_09
Patent number
US08022206B2

Reaction notes

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