Methyl Acetate → HCID 131717673, compound

HRID 1609546Notes

Reaction equation

HRID 1609546 reaction equation
[C:1]([O:4][CH3:5])(=[O:3])[CH3:2].[H-].[Na+].C([Li])CCC.[C:13]([C:17]1[C:18]([C:38]2[CH:43]=[CH:42][C:41]([F:44])=[CH:40][CH:39]=2)=[C:19](/[CH:34]=[CH:35]/[CH:36]=[O:37])[CH:20]([CH:31]([CH3:33])[CH3:32])[N:21]([CH2:26][O:27][SiH:28]([CH3:30])[CH3:29])[C:22]=1[CH:23]([CH3:25])[CH3:24])([CH3:16])([CH3:15])[CH3:14].[O:45]1CC[CH2:47][CH2:46]1>CCCCCC.O.C(O)(=O)C>[C:13]([C:17]1[C:18]([C:38]2[CH:39]=[CH:40][C:41]([F:44])=[CH:42][CH:43]=2)=[C:19](/[CH:34]=[CH:35]/[CH:36]([OH:37])[CH2:47][C:46](=[O:45])[CH2:2][C:1]([O:4][CH3:5])=[O:3])[CH:20]([CH:31]([CH3:33])[CH3:32])[N:21]([CH2:26][O:27][SiH:28]([CH3:29])[CH3:30])[C:22]=1[CH:23]([CH3:25])[CH3:24])([CH3:14])([CH3:16])[CH3:15]

Participants

9

Reactant 5

HCID 6584Methyl AcetateHCID 8028Tetrahydrofuran3×HCID 24758Sodium hydrideHCID 131717674HCID 131717674, compoundHCID 178418339Butyllithium

Product 1

HCID 131717673HCID 131717673, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 8058HexaneSolvent

Procedure

1.02 g (8.8 mmol) of methyl acetate in 5 ml of dry tetrahydrofuran are added dropwise under nitrogen to a suspension of 330 mg (11 mmol) of 80% strength sodium hydride in 30 ml of dry tetrahydrofuran at -5° C. After 15 min, 5.5 ml (8.8 mmol) of 15% strength butyllithium in n-hexane ere added dropwise at the same temperature and the mixture is stirred for 15 minutes. Subsequently, 2 g (4.4 mmol) of the compound from Example 8 dissolved in 20 ml of dry tetrahydrofuran are added dropwise and the mixture is stirred for 30 minutes at -5° C. 3 ml of 50% strength acetic acid are cautiously added to the reaction solution, and the mixture is diluted using 100 ml of water and extracted three times using 100 ml of ether each time. The combined organic phases are washed twice with saturated sodium hydrogen carbonate solution and once with saturated sodium chloride solution, dried over magnesium sulphate and concentrated in vacuo. The residue is chromatographed on a column (100 g of silica gel 70-230 mesh, φ3 cm, using ethyl acetate/petroleum ether 3:7).

Workup

  1. additionare added dropwise
  2. stirringthe mixture is stirred for 30 minutes at -5° C
  3. additionthe mixture is diluted
  4. extractionextracted three times
  5. washThe combined organic phases are washed twice with saturated sodium hydrogen carbonate solution and once with saturated sodium chloride solution
  6. dry with materialdried over magnesium sulphate
  7. concentrationconcentrated in vacuo
  8. customThe residue is chromatographed on a column (100 g of silica gel 70-230 mesh, φ3 cm, using ethyl acetate/petroleum ether 3:7)

Sources & evidence

ORD record
ord-d3887f627e164632b5dc8db6c5a562d2
Source dataset
uspto-grants-1995_03
Patent number
US05401746

Reaction notes

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