Ethyl Acetate → HCID 68233570, compound

HRID 1429401Notes

Reaction equation

HRID 1429401 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH2:10][CH2:11][CH2:12][C:13]1[CH:22]=[CH:21][CH:20]=[CH:19][C:14]=1[C:15](OC)=[O:16])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3].CC(=O)OCC>C1COCC1>[C:1]([O:5][C:6](=[O:7])[NH:8][CH:9]([CH2:10][CH2:11][CH2:12][C:13]1[CH:22]=[CH:21][CH:20]=[CH:19][C:14]=1[CH2:15][OH:16])[CH2:23][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 21226445Aluminium lithium hydrideHCID 67391159HCID 67391159, compound

Product 1

HCID 68233570HCID 68233570, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

30h (1.8 g, 4.55 mmol) in THF (5 mL) was added dropwise to a stirred solution of LiAlH4 (0.35 g, 9.1 mmol) in THF (25 mL) at 0° C. Then the mixture was stirred at rt until TLC analysis indicated the total consumption of the SM. The reaction was quenched carefully by the slow addition of water (10 mL), and then the liquid was decanted away from the precipitate. The precipitate was washed with DCM (3×50 mL) and the organic layers were combined and dried over Na2SO4. The solvent was removed and the residue was purified by CC using PE:EA=5:1 as mobile phase to afford the desired product (1.3 g, 79% yield).

Workup

  1. customthe total consumption of the SM
  2. customThe reaction was quenched carefully by the slow addition of water (10 mL)
  3. customthe liquid was decanted away from the precipitate
  4. washThe precipitate was washed with DCM (3×50 mL)
  5. dry with materialdried over Na2SO4
  6. customThe solvent was removed
  7. customthe residue was purified by CC

Sources & evidence

ORD record
ord-8b6fa7c89bcb4790b1b1153223c9dae1
Source dataset
uspto-grants-2015_01
Patent number
US08940722B2

Reaction notes

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