Sodium Methoxide → HCID 44815554, compound

HRID 1879089Notes

Reaction equation

HRID 1879089 reaction equation
[CH3:1][C:2]1([C:11]#[C:12][Si](C)(C)C)[CH2:10][C:6]2[CH:7]=[N:8][O:9][C:5]=2[CH:4]=[CH:3]1.C[O-].[Na+]>CCOCC.CO.C(Cl)Cl.CCOCC>[C:11]([C:2]1([CH3:1])[CH2:10][CH:6]([C:7]#[N:8])[C:5](=[O:9])[CH:4]=[CH:3]1)#[CH:12]

Participants

6

Reactant 2

HCID 10942334Sodium MethoxideHCID 57523584HCID 57523584, compound

Product 1

HCID 44815554HCID 44815554, compoundYield 100.1%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 21881112Ethyl ether methylene chlorideSolvent

Procedure

To a solution of 9 (75 mg, 0.32 mmol) in dry ether (7.4 mL) was added a solution of sodium methoxide (565 mg) in dry methanol (6 mL). The mixture was stirred at room temperature for 1 h. The mixture was diluted with methylene chloride/ether (1:2, 40 mL). The mixture was washed with 5% aqueous HCl solution (10 mL×2). The acidic washings were extracted with methylene chloride/ether (1:2, 10 mL×1). The original organic solution and the extract were combined. The combined solution was washed with water (15 mL×2) and brine (15 mL×1), dried over MgSO4, and filtered. The filtrate was evaporated in vacuo to give MCE-4 as a crystalline solid (51 mg, quantitative yield). This material was used without further purification for the next step.

Workup

  1. washThe mixture was washed with 5% aqueous HCl solution (10 mL×2)
  2. extractionThe acidic washings were extracted with methylene chloride/ether (1:2, 10 mL×1)
  3. washThe combined solution was washed with water (15 mL×2) and brine (15 mL×1)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customThe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-6396fc23d13641ceaeb34a0401fe4ec1
Source dataset
uspto-grants-2012_11
Patent number
US08314137B2

Reaction notes

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