Methanol → HCID 86679296, compound

HRID 1519738Notes

Reaction equation

HRID 1519738 reaction equation
C(=O)([O-])[O-].[K+].[K+].CO.[CH3:9][O:10][CH2:11][CH2:12][CH2:13]/[CH:14]=[CH:15]/[C:16]#[C:17][Si](C)(C)C.[Cl-].[NH4+]>C(OCC)C>[CH3:9][O:10][CH2:11][CH2:12][CH2:13]/[CH:14]=[CH:15]/[C:16]#[CH:17]

Participants

6

Reactant 4

HCID 887MethanolHCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 86679297HCID 86679297, compound

Product 1

HCID 86679296HCID 86679296, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Potassium carbonate (0.10 g) was added, under ice cooling, to a methanol (3.7 mL) solution of ((E)-7-methoxyhept-3-en-1-yn-1-yl)trimethylsilane (0.74 g) as obtained in Example 25-(1), and the mixture was stirred for 45 minutes at room temperature. Diethyl ether and an aqueous solution of ammonium chloride were added to isolate the organic layer. The extract was washed with brine, and dried over anhydrous magnesium sulfate. Then, the desiccant was filtered out, and the solvent was distilled off under reduced pressure to obtain (E)-7-methoxyhept-3-en-1-yn (pale yellow oil) (0.34 g, 73%).

Workup

  1. customto isolate the organic layer
  2. washThe extract was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationThen, the desiccant was filtered out
  5. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-81a210ad1bbe45e2bbfca5b1e50b5e7a
Source dataset
uspto-grants-2015_07
Patent number
US09073821B2

Reaction notes

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