Sodium borohydride → HCID 86680627, compound

HRID 1497459Notes

Reaction equation

HRID 1497459 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[CH:11][C:12]([C:15](=[O:17])[CH3:16])=[N:13][CH:14]=2)=[CH:5][CH:4]=1.[BH4-].[Na+]>C1COCC1.CO.O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:10]=[CH:11][C:12]([CH:15]([OH:17])[CH3:16])=[N:13][CH:14]=2)=[CH:7][CH:8]=1

Participants

6

Reactant 2

HCID 4311764Sodium borohydrideHCID 11195507HCID 11195507, compound

Product 1

HCID 86680627HCID 86680627, compoundYield 66.1%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 1-(5-(4-methoxyphenyl)pyridin-2-yl)ethanone (1.5 g, 6.6 mmol) in THF (8 mL) and methanol (8 mL) was added NaBH4 (0.4 g, 13.2 mmol) at 0° C. and the reaction was stirred at rt for about 1 h. The reaction mixture was diluted with water (100 mL), extracted with ethylacetate (2×100 mL). The combined organic extracts were washed with brine solution (10 mL), organic layer was dried over Na2SO4 and concentrated under vacuum to obtain 1-(5-(4-methoxyphenyl)-pyridin-2-yl)ethanol as an off-white solid (1.0 g, 66% yield). 1H NMR (400 MHz, DMSO-d6): 8.72 (d, 1H), 7.84 (dd, 1H), 7.51 (d, 2H), 7.32 (d, 1H), 7.01 (d, 2H), 4.93 (s, 1H), 4.11 (d, 1H), 3.86 (s, 3H), 1.54 (d, 3H), LC-MS m/z calcd for [M+H]+ 230.1. found 230.3.

Workup

  1. extractionextracted with ethylacetate (2×100 mL)
  2. washThe combined organic extracts were washed with brine solution (10 mL), organic layer
  3. dry with materialwas dried over Na2SO4
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-3f930a966336489c829285cde5033177
Source dataset
uspto-grants-2015_12
Patent number
US09199975B2

Reaction notes

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