Aluminium lithium hydride → HCID 86635371, compound

HRID 657149Notes

Reaction equation

HRID 657149 reaction equation
[Cl:1][C:2]1[C:7]([CH2:8][CH2:9][C:10](OCC)=[O:11])=[C:6]([Cl:15])[N:5]=[C:4](/[CH:16]=[CH:17]/[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[Cl:15][C:6]1[C:7]([CH2:8][CH2:9][CH2:10][OH:11])=[C:2]([Cl:1])[N:3]=[C:4](/[CH:16]=[CH:17]/[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:5]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 86628367HCID 86628367, compound

Product 1

HCID 86635371HCID 86635371, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To Ethyl 3-{4,6-dichloro-2-[(E)-2-phenylethenyl]-5-pyrimidinyl}propanoate (0.35 g, 1.04 mmol) in THF (10 mL) at −78° C. was added a 1N solution of lithium aluminium hydride in THF (2.0 mL, 2.0 mmol). The reaction was allowed to stir under nitrogen for 1 h and allowed to warm to 0° C. After 2 h at 0° C. the reaction was quenched by addition of 5 mL of methanol and 2 mL of water. The reaction was concentrated under vacuum and the residue was partitioned between EtOAc and brine. The aqueous layer was extracted with EtOAc (3×), dried over Na2SO4, filtered and concentrated under vacuum to give the product as a yellow solid (275 mg, 86%) to be used without further purification.

Workup

  1. customAfter 2 h at 0° C. the reaction was quenched by addition of 5 mL of methanol and 2 mL of water
  2. concentrationThe reaction was concentrated under vacuum
  3. customthe residue was partitioned between EtOAc and brine
  4. extractionThe aqueous layer was extracted with EtOAc (3×)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-8cd664ce2c434fa58b0cae46508b035a
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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