Tetrahydrofuran → HCID 22504045, compound

HRID 1814323Notes

Reaction equation

HRID 1814323 reaction equation
C[O:2][C:3](=O)[CH2:4][C:5]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:6]=1[CH:7]=[CH:8][C:9]([Cl:15])=[N:10]2.C1COCC1.[H-].[H-].[H-].[H-].[Li+].[Al+3].C(OCC)(=O)C>CCOCC>[Cl:15][C:9]1[CH:8]=[CH:7][C:6]2[C:11](=[CH:12][CH:13]=[CH:14][C:5]=2[CH2:4][CH2:3][OH:2])[N:10]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8857Ethyl AcetateHCID 21226445Aluminium lithium hydrideHCID 86588219HCID 86588219, compound

Product 1

HCID 22504045HCID 22504045, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-20 °C

Procedure

A mixture of 0.35 g (1.46 mmol) (2-chloro-quinolin-5-yl)-acetic acid methyl ester and 10 mL anhydrous THF was cooled to −20° C. in a dry ice/acetone bath. 1.4 mL (1.4 mmol) IM LiAlH4 solution in ether was added dropwise. After 10 min, TLC analysis (ethyl acetate, silica, Rf prod 0.3) showed starting material consumed. The reaction was quenched with 1 mL of 1M aqueous potassium sodium tartrate solution. The product was partitioned between ethyl acetate and 10 ml brine and the product extracted with three 25 mL portions of ethyl acetate. The combined organic extracts were washed with 25 mL of brine, dried over magnesium sulfate, filtered, and the solvent removed under reduced pressure to yield 0.29 g (1.37 mmol 99.9%) of 2-(2-chloro-quinolin-5-yl)-ethanol as a white solid. MS(APCI) m/z 208 (M, 100% abundance), 210 (M+2, 32% abundance). 1H NMR (400 MHz) CDCl3 8.38 (d, J=8.9 Hz, 1H), 7.92 (d, J=8.5 Hz, 1H), 7.70 (m, 1H), 7.46 (d, J=7.2 Hz, 1H), 7.41 (d, J=8.9 Hz), 3.97 (m, 2H), 3.32 (t, J=6.5 Hz, 2H), 1.45 (m, 1H).

Workup

  1. customconsumed
  2. customThe reaction was quenched with 1 mL of 1M aqueous potassium sodium tartrate solution
  3. customThe product was partitioned between ethyl acetate and 10 ml brine
  4. extractionthe product extracted with three 25 mL portions of ethyl acetate
  5. washThe combined organic extracts were washed with 25 mL of brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-0aa6bf2ebbfd484fbcdb474a91d8e30e
Source dataset
uspto-grants-2005_04
Patent number
US06875765B2

Reaction notes

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