Methanol → 2-(Quinolin-5-yl)ethan-1-ol

HRID 1814300Notes

Reaction equation

HRID 1814300 reaction equation
[CH2:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7][CH:8]=[N:9]2)[CH:2]=C.C(Cl)Cl.[BH4-].[Na+].C[OH:20]>>[N:9]1[C:10]2[C:5](=[C:4]([CH2:1][CH2:2][OH:20])[CH:13]=[CH:12][CH:11]=2)[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 4

HCID 887MethanolHCID 6344DichloromethaneHCID 4311764Sodium borohydrideHCID 225041105-(2-Propen-1-yl)quinoline

Product 1

HCID 225041322-(Quinolin-5-yl)ethan-1-olYield 50%

Procedure

5-Allyl-quinoline (3.12 g, 18.4 mmol) was dissolved in 40 mL methanol and 40 mL methylene chloride and cooled to −78° C. Ozone was bubbled in until a green solution was seen. Sodium borohydride (1.4 g, 36.8 mmol) was added. The reaction was warmed to room temperature and stirred for 2 hours. The reaction was quenched with water. A saturated solution of KHPO4 was added and the mixture extracted with methylene chloride. The organic extracts were dried with Na2SO4, filtered, and concentrated in vacuo. The crude product was chromatographed with ethyl acetate to yield 1.6 g (50%) of 2-quinolin-5-yl-ethanol as a yellow solid. MS (APCI) m/z 174.1 (M+1).

Workup

  1. customOzone was bubbled in until a green solution
  2. customThe reaction was quenched with water
  3. additionA saturated solution of KHPO4 was added
  4. extractionthe mixture extracted with methylene chloride
  5. dry with materialThe organic extracts were dried with Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product was chromatographed with ethyl acetate

Sources & evidence

ORD record
ord-49d5dbc8d34b426d8bfb9fe3cb872e4b
Source dataset
uspto-grants-2005_04
Patent number
US06875765B2

Reaction notes

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