Ethyl Acetate → HCID 21835237, compound

HRID 1741282Notes

Reaction equation

HRID 1741282 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[CH:7]([CH3:13])[C:8](OCC)=[O:9].[H-].C([Al+]CC(C)C)C(C)C.[NH4+].[Cl-].CCOC(C)=O>C1COCC1>[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[CH:7]([CH3:13])[CH2:8][OH:9]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 21225700DiisobutylaluminumhydrideHCID 21835141HCID 21835141, compound

Product 1

HCID 21835237HCID 21835237, compoundYield 43.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of ethyl 2-(pyrimidin-2-yl)propanoate (1.7 g, 9.4 mmol) in THF (100 ml) at 0° C., was added diisobutylaluminium hydride (23.6 ml of a 1.0 M solution in THF, 23.6 mmol) dropwise. After 3 h NH4Cl (sat., 30 ml) was added and the mixture stirred at room temperature for 30 min. EtOAc (100 ml) was added and the mixture filtered. The filtrate was dried (Na2SO4) and evaporated. The residue was chromatographed on silica, eluting with CH2Cl2 :MeOH (95:5), to give the alcohol (562 mg, 43%) as a pale yellow oil. 1H NMR (360 MHz, CDCl3) δ 1.38 (3H, d, J=7.2 Hz), 3.22-3.31 (1H, m), 3.65 (1H, br s), 3.80-4.05 (2H, m), 7.18 (1H, t, J=4.9 Hz), 8.72 (2H, d, J=4.9 Hz).

Workup

  1. filtrationthe mixture filtered
  2. dry with materialThe filtrate was dried (Na2SO4)
  3. customevaporated
  4. customThe residue was chromatographed on silica
  5. washeluting with CH2Cl2 :MeOH (95:5)

Sources & evidence

ORD record
ord-287e542a76d34765bb880677b8b71f17
Source dataset
uspto-grants-1999_10
Patent number
US05973156

Reaction notes

Loading…