1,2-Dimethoxyethane → HCID 21528002, compound

HRID 1658569Notes

Reaction equation

HRID 1658569 reaction equation
[CH:1]#[C:2][CH2:3][CH:4]([OH:9])[CH2:5][CH2:6][CH2:7][CH3:8].[CH3:10]OCCOC.C([Li])CCC>CCCCCC.CCOCC>[CH3:10][O:9][CH:4]([CH2:5][CH2:6][CH2:7][CH3:8])[CH2:3][C:2]#[CH:1]

Participants

6

Reactant 3

HCID 80711,2-DimethoxyethaneHCID 1036561-Octyn-4-olHCID 178418339Butyllithium

Product 1

HCID 21528002HCID 21528002, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8058HexaneSolvent

Procedure

To a solution of 1.26 parts of 1-octyn-4(RS)-ol in 10 parts by volume of ethylene glycol dimethyl ether, cooled to about -40° is added dropwise 4 parts by volume of 2.5 M n-butyl lithium in hexane. The cooling bath is removed and 4 parts of trimethyloxonium hexafluorophosphate is added. The resulting reaction mixture is stirred at room temperature for about 1 hour, then is diluted with ether, washed successively with dilute hydrochloric acid and water, dried over anhydrous sodium sulfate and stripped of solvent under reduced pressure to afford 1-octyn-4(RS)-ol methyl ether.

Workup

  1. customThe cooling bath is removed
  2. addition4 parts of trimethyloxonium hexafluorophosphate is added
  3. customThe resulting reaction mixture
  4. washwashed successively with dilute hydrochloric acid and water
  5. dry with materialdried over anhydrous sodium sulfate

Sources & evidence

ORD record
ord-4e0ece6792254fbb8524510e5281005f
Source dataset
uspto-grants-1976_06
Patent number
US03965143

Reaction notes

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