Tetrahydrofuran → Ethyl 3-(2,6-dichloropyridin-3-yl)propan-1-ol

HRID 595739Notes

Reaction equation

HRID 595739 reaction equation
[Cl:1][C:2]1[C:7]([CH2:8][CH2:9][C:10]([O:12]CC)=O)=[CH:6][CH:5]=[C:4]([Cl:15])[N:3]=1.[Li+].[BH4-].[CH2:18]1COC[CH2:19]1>>[CH2:18]([CH:10]([OH:12])[CH2:9][CH2:8][C:7]1[C:2]([Cl:1])=[N:3][C:4]([Cl:15])=[CH:5][CH:6]=1)[CH3:19]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 4148881Lithium borohydrideHCID 23157101Ethyl 3-(2,6-dichloropyridin-3-yl)propanoate

Product 1

HCID 118573558Ethyl 3-(2,6-dichloropyridin-3-yl)propan-1-ol

Conditions

Temperature
0 °C

Procedure

To a solution of ethyl 3-(2,6-dichloropyridin-3-yl)propanoate in THF (12 mL) was added LiBH4 (88 mg, 4.03 mmol). The resultant mixture was stirred at ambient temperature for 2.5 h then was cooled to 0° C. and carefully quenched by addition of saturated NH4Cl(aq) solution. The reaction mixture was diluted with EtOAc and the organic layer washed successively with H2O (1×) and brine (1×). The organic extract was dried over MgSO4, filtered, and concentrated in vacuo. Purification by silica gel column chromatography using a gradient of 0-60% EtOAc/Hexanes as eluent provided the title compound. 1H NMR δ (ppm) (CHCl3-d): 7.58 (1H, d, J=7.92 Hz), 7.25 (1H, d, J=7.80), 3.73 (2H, q, J=5.48 Hz), 2.85 (2H, t, J=7.76 Hz), 1.95˜1.88 (2H, m), 1.42 (1H, m). MS (M+H)+: 205.

Workup

  1. customcarefully quenched by addition of saturated NH4Cl(aq) solution
  2. additionThe reaction mixture was diluted with EtOAc
  3. washthe organic layer washed successively with H2O (1×) and brine (1×)
  4. extractionThe organic extract
  5. dry with materialwas dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customPurification by silica gel column chromatography

Sources & evidence

ORD record
ord-d873d83bbfa14e2a8f7c4332fba066b7
Source dataset
uspto-grants-2016_01
Patent number
US09243002B2

Reaction notes

Loading…