Water → HCID 14726531, compound

HRID 1742390Notes

Reaction equation

HRID 1742390 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:13][N:12]=[C:11]([C:14]3[CH:23]=[CH:22][C:21]4[C:20]([CH3:25])([CH3:24])[CH2:19][CH2:18][C:17]([CH3:27])([CH3:26])[C:16]=4[CH:15]=3)[CH:10]=2)=[CH:5][CH:4]=1)#[N:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].O>CCOCC>[NH2:2][CH2:1][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[O:13][N:12]=[C:11]([C:14]3[CH:23]=[CH:22][C:21]4[C:20]([CH3:25])([CH3:24])[CH2:19][CH2:18][C:17]([CH3:27])([CH3:26])[C:16]=4[CH:15]=3)[CH:10]=2)=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14726525HCID 14726525, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 14726531HCID 14726531, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

0.95 g (2.7 millimoles) of 5-(4-cyanophenyl)-3-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-isoxazole (Example 19) were added a little at a time, at room temperature, to a suspension of 0.28 g (7.4 millimoles) of lithium aluminum hydride in 30 ml of dry ether. The mixture was then refluxed for 3 hours and cooled, after which hydrolysis was carried out carefully with water, the phases were separated, the aqueous phase was extracted again with ether and the combined organic extracts were dried over sodium sulfate and evaporated down. 0.9 g of the title compound of melting point 138°-143° C. remained as the residue.

Workup

  1. temperatureThe mixture was then refluxed for 3 hours
  2. temperaturecooled
  3. customafter which hydrolysis
  4. customthe phases were separated
  5. extractionthe aqueous phase was extracted again with ether
  6. dry with materialthe combined organic extracts were dried over sodium sulfate
  7. customevaporated down

Sources & evidence

ORD record
ord-9c8307d578444f1cbb06cb969d02dd79
Source dataset
uspto-grants-1994_08
Patent number
US05338749

Reaction notes

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