Diethyl Ether → HCID 22504174, compound

HRID 1814373Notes

Reaction equation

HRID 1814373 reaction equation
CO[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]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[N:10]2.[H-].[Al+3].[Li+].[H-].[H-].[H-].CC[O:32]CC>>[CH2:16]([O:15][C:9]1[CH:8]=[CH:7][C:6]2[C:11](=[CH:12][CH:13]=[CH:14][C:5]=2[CH:4]([OH:32])[CH3:3])[N:10]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 3

HCID 3283Diethyl EtherHCID 21226445Aluminium lithium hydrideHCID 69692935HCID 69692935, compound

Product 1

HCID 22504174HCID 22504174, compound

Conditions

Temperature
-10 °C

Procedure

(2-Benzyloxy-quinolin-5-yl)-acetic acid methyl ester (0.198 g, 0.64 mmol) was dissolved in 10 mL of anhydrous ether, and cooled to −10° C. Lithium aluminum hydride (1.0M solution in ether, 0.5 mL, 0.5 mmol) was added and stirred at −10° C. for 1 h. The reaction was quenched with 0.5 mL water, then 0.5 mL 15% NaOH, then 1.5 mL water. A solution of Na, K tartrate was added to help solublized the salts. Ethyl acetate was added and the layers were separated. The aqueous layer was washed with ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulfate, filtered, and rotovapped. (2-Benzyloxy-quinolin-5-yl)-ethanol (0.140 g, 78%) was used without further purification. MS m/z 280 (M+1).

Workup

  1. customThe reaction was quenched with 0.5 mL water
  2. additionA solution of Na, K tartrate was added
  3. additionEthyl acetate was added
  4. customthe layers were separated
  5. washThe aqueous layer was washed with ethyl acetate
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. custom(2-Benzyloxy-quinolin-5-yl)-ethanol (0.140 g, 78%) was used without further purification

Sources & evidence

ORD record
ord-557e3ac362e1440eb3f8a13d4bcee052
Source dataset
uspto-grants-2005_04
Patent number
US06875765B2

Reaction notes

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