Sodium borohydride → 8-Chloro-1,2,3,4-tetrahydronaphthalen-1-ol

HRID 912033Notes

Reaction equation

HRID 912033 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[C:10](=[O:12])[CH2:9][CH2:8][CH2:7]2.[BH4-].[Na+]>CO>[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH:10]([OH:12])[CH2:9][CH2:8][CH2:7]2

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 113673658-Chloro-3,4-dihydro-2H-naphthalen-1-one

Product 1

HCID 578125228-Chloro-1,2,3,4-tetrahydronaphthalen-1-ol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of 8-chloro-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 two rounds of pTLC [Silicycle, 20×20 plate, 1000 μm, one development in neat CH2Cl2], giving the title material as an off-white solid. 1H NMR (400 MHz, CDCl3) δ=1.72-1.85 (m, 2H), 1.92-2.05 (m, 1H), 2.16-2.24 (m, 1H), 2.38 (dd, J=3.8, 1.3 Hz, 1H), 2.71 (ddd, J=17.7, 12.1, 5.8 Hz, 1H), 2.82-2.92 (m, 1H), 5.09 (q, J=3.5 Hz, 1H), 7.06 (d, J=7.6 Hz, 1H), 7.15 (dd, J=7.7, 7.7 Hz, 1H), 7.24 (d, J=7.8 Hz, 1H). MS (ES+): m/z 164.98/166.98 (100/53) [MH+−H2O]. HPLC: tR=3.14 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 two rounds of pTLC [Silicycle, 20×20 plate, 1000 μm, one development in neat CH2Cl2]

Sources & evidence

ORD record
ord-de255d2595294bccbac4d6cf811271a3
Source dataset
uspto-grants-2011_09
Patent number
US08022206B2

Reaction notes

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