Triethylamine → HCID 57062055, compound

HRID 462383Notes

Reaction equation

HRID 462383 reaction equation
[Si:1]([O:8][CH2:9][CH2:10][C:11]#[C:12][CH2:13][CH2:14][OH:15])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:23][S:24](Cl)(=[O:26])=[O:25]>C(Cl)Cl.O>[CH3:23][S:24]([O:15][CH2:14][CH2:13][C:12]#[C:11][CH2:10][CH2:9][O:8][Si:1]([C:4]([CH3:6])([CH3:7])[CH3:5])([CH3:3])[CH3:2])(=[O:26])=[O:25]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 23253892HCID 23253892, compound

Product 1

HCID 57062055HCID 57062055, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
-20 °C

Procedure

A solution of 3.9 g of 3-hexyn-1,6-diol mono-t-butyl-dimethylsilyl ether in 50 ml of methylene chloride was cooled to -20° C. and treated with 4.18 ml of triethyl amine and then 1.77 ml of methane sulfonyl chloride. After stirring 15 minutes at -20° C. the reaction mixture was diluted with water and extracted twice with 50 ml of methylene chloride. The organic layers were washed with brine, dried over sodium sulfate and evaported in vacuo to give the 3-hexyn-1,6-diol t-butyldimethylsilyl ether methyl sulfonate.

Workup

  1. extractionextracted twice with 50 ml of methylene chloride
  2. washThe organic layers were washed with brine
  3. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-c53ad314eb8446d08c46165a390e3a15
Source dataset
uspto-grants-1985_05
Patent number
US04515727

Reaction notes

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