Aluminium lithium hydride → HCID 86756061, compound

HRID 1858329Notes

Reaction equation

HRID 1858329 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][O:8][C:9]1[CH:28]=[CH:27][C:12]([CH2:13][O:14][C:15]2[C:20]([C:21](OCC)=[S:22])=[CH:19][N:18]=[C:17]([CH3:26])[N:16]=2)=[CH:11][CH:10]=1>O1CCCC1.[O-2].[O-2].[Mn+4]>[CH3:7][O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:13][O:14][C:15]2[C:20]([CH:21]=[S:22])=[CH:19][N:18]=[C:17]([CH3:26])[N:16]=2)=[CH:27][CH:28]=1

Participants

5

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 86756060HCID 86756060, compound

Product 1

HCID 86756061HCID 86756061, compoundYield 100.7%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

An ice-cooled suspension of 1.6 g (42 mmol) of lithium aluminium hydride in 150 ml of tetrahydrofuran was treated slowly with a solution of 14 g (42 mmol) of ethyl 4-(4-methoxy-benzyloxy)-2-methylthiopyrimidine-5-carboxylate in 150 ml of tetrahydrofuran. After 15 minutes the reaction was quenched by the cautious addition of 1.5 ml of water, 0.8 ml of 2M aqueous sodium hydroxide and 2.3 ml of water. The resulting suspension was filtered through hyflo filter aid. The filtered solid was washed thoroughly with tetrahydrofuran and the combined filtrate and washings evaporated. The residue was partitioned between 200 ml of dichloromethane and 100 ml of water. The organic phase was dried over magnesium sulfate and filtered. To the filtrate was added a further 100 ml of dichloromethane which was then treated with 36 g (414 mmol) of manganese dioxide. The mixture was stirred at ambient temperature for 2 hours and filtered through hyflo filter aid. The filtrate was evaporated to give 11.6 g (95%) of 4-(4-methoxy-benzyloxy)-2-methylthiopyrimidine-5-carboxaldehyde as a pale yellow oil. [Mass spectrum (ESI) MH+ =291].

Workup

  1. customAfter 15 minutes the reaction was quenched by the cautious addition of 1.5 ml of water, 0.8 ml of 2M aqueous sodium hydroxide and 2.3 ml of water
  2. filtrationThe resulting suspension was filtered through hyflo
  3. filtrationfilter aid
  4. washThe filtered solid was washed thoroughly with tetrahydrofuran
  5. customthe combined filtrate and washings evaporated
  6. customThe residue was partitioned between 200 ml of dichloromethane and 100 ml of water
  7. dry with materialThe organic phase was dried over magnesium sulfate
  8. filtrationfiltered
  9. additionTo the filtrate was added a further 100 ml of dichloromethane which
  10. filtrationfiltered through hyflo
  11. filtrationfilter aid
  12. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-0419d33bacf44ecd89974b71611de4b2
Source dataset
uspto-grants-2000_11
Patent number
US06150373

Reaction notes

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