HCID 19041803, compound → HCID 19041747, compound

HRID 1684051Notes

Reaction equation

HRID 1684051 reaction equation
[C:1]([C:3]1[C:4]([O:16][CH3:17])=[C:5]([O:14][CH3:15])[CH:6]=[C:7]([CH:9]2[O:13][CH2:12][CH2:11][O:10]2)[CH:8]=1)#[N:2].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1.C(OCC)C>[NH2:2][CH2:1][C:3]1[C:4]([O:16][CH3:17])=[C:5]([O:14][CH3:15])[CH:6]=[C:7]([CH:9]2[O:13][CH2:12][CH2:11][O:10]2)[CH:8]=1

Participants

5

Reactant 2

HCID 19041803HCID 19041803, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 19041747HCID 19041747, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

2-(5-cyano-3,4-dimethoxyphenyl)-1,3-dioxolane (50) (FIG. 22) (0.555 g, 2.23 mmole) was predissolved in 2 ml dry THF and 10 ml anhydrous diethyl ether. To this solution under an argon atmosphere at room temperature was added 2.23 ml of 1.0M lithium aluminum hydride in diethyl ether solution. The reaction was then stirred at room temperature for 4 hours. The reaction was then cooled to 0° C. and the excess hydride destroyed with H2O. The reaction mixture was subsequently quenched with 10% NaOH and extracted with diethyl ether. The organic layer was dried over MgSO4, and concentrated to an oil in vacuo.

Workup

  1. temperatureThe reaction was then cooled to 0° C.
  2. customthe excess hydride destroyed with H2O
  3. customThe reaction mixture was subsequently quenched with 10% NaOH
  4. extractionextracted with diethyl ether
  5. dry with materialThe organic layer was dried over MgSO4
  6. concentrationconcentrated to an oil in vacuo

Sources & evidence

ORD record
ord-c347d85011b44a148db4ed7800bf12de
Source dataset
uspto-grants-1997_06
Patent number
US05639782

Reaction notes

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