Diethyl Ether → HCID 15029617, compound

HRID 893086Notes

Reaction equation

HRID 893086 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][O:8][C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]=1[CH:19]([S:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH2:20][N+:21]([O-])=O.CCOCC>CCOCC.C1COCC1>[CH3:7][O:8][C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]=1[CH:19]([S:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH2:20][NH2:21]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 15029616HCID 15029616, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 15029617HCID 15029617, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 21868444Ether tetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a vigorously stirred suspension of lithium aluminum hydride (76 mg. 20 mmol) in anhydrous ether - THF 2:1 solvent mixture (80 ml) a solution of 1-(2-methoxynaphth-1-yl)-1-(phenylthio)-2-nitroethane (3394 mg, 10 mmol) in ether- THF 2:1 (40 ml) is added dropwise. The reaction mixture is heated at reflux for 24 h and then cooled to 0° C. Ether is added and the excess of LiAlH4 is destroyed by the cautious successive addition of water (2 ml) and 2N NaOH solution (4 ml). The aluminum salts are filtered off and the organic layer evaporated in vacuo. The residue is dissolved in ether and the ethereal solution extracted with 2N HCl solution. The aqueous acidic layer is brought to pH 9 by addition of 2N NaOH and extracted with ether. The ethereal layer is dried with Na2SO4 and then evaporated to dryness in vacuo to give almost pure title compound in 70 % yield (2165 mg).

Workup

  1. additionis added dropwise
  2. temperatureThe reaction mixture is heated
  3. temperatureat reflux for 24 h
  4. customthe excess of LiAlH4 is destroyed by the cautious successive addition of water (2 ml) and 2N NaOH solution (4 ml)
  5. filtrationThe aluminum salts are filtered off
  6. customthe organic layer evaporated in vacuo
  7. dissolutionThe residue is dissolved in ether
  8. extractionthe ethereal solution extracted with 2N HCl solution
  9. additionThe aqueous acidic layer is brought to pH 9 by addition of 2N NaOH
  10. extractionextracted with ether
  11. dry with materialThe ethereal layer is dried with Na2SO4
  12. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-135dd4511a094b51a13e5bb92b02ac34
Source dataset
uspto-grants-1992_06
Patent number
US05122537

Reaction notes

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