Aluminium lithium hydride → HCID 66749674, compound

HRID 2401889Notes

Reaction equation

HRID 2401889 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][C:24]=1[Cl:25])[CH2:5][C:6]1[N:7]=[C:8]([N:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)[S:9][C:10]=1[C:11](OCC)=[O:12].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][C:24]=1[Cl:25])[CH2:5][C:6]1[N:7]=[C:8]([N:16]2[CH2:17][CH2:18][O:19][CH2:20][CH2:21]2)[S:9][C:10]=1[CH2:11][OH:12]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 66748191HCID 66748191, compound

Product 1

HCID 66749674HCID 66749674, compoundYield 65.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of ethyl 4-(3,4-dichlorobenzyl)-2-morpholinothiazole-5-carboxylate (4.92 g, 12.2 mmol) in THF (100 mL) was added a 2.00 M solution of LAH in THF (12.9 mL, 25.8 mmol) and the resulting solution was stirred for 2 hours at room temperature. The reaction was quenched by adding saturated NH4Cl (26 mL) followed by 1M HCl (26 mL). Water (100 mL) and ethyl acetate (200 mL) were then added. The layers were separated and the organic layer was washed with brine (50 mL). The organic layer was dried and concentrated in vacuo. The residue was purified by silica gel chromatography (ethyl acetate/DCM=0/100→100/0) to give 2.87 g (65% yield) of the title compound as a white solid. LC/MS (FA) ES+ 359, 361. 1H NMR (400 MHz, CDCl3) δ: 7.34-7.31 (m, 2H), 7.09 (dd, 1H, J=6.0, 2.0 Hz), 4.66 (d, 2H, J=1.2 Hz), 3.84 (s, 2H), 3.79-3.77 (m, 4H), 3.42-3.39 (m, 4H).

Workup

  1. customThe reaction was quenched
  2. additionby adding saturated NH4Cl (26 mL)
  3. additionWater (100 mL) and ethyl acetate (200 mL) were then added
  4. customThe layers were separated
  5. washthe organic layer was washed with brine (50 mL)
  6. customThe organic layer was dried
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by silica gel chromatography (ethyl acetate/DCM=0/100→100/0)

Sources & evidence

ORD record
ord-7b575610a6774678b37a289580570761
Source dataset
uspto-grants-2014_08
Patent number
US08796268B2

Reaction notes

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