Triethylamine → HCID 86674468, compound

HRID 75176Notes

Reaction equation

HRID 75176 reaction equation
[CH3:1][C:2]([CH3:21])([Si:4]([CH3:20])([CH3:19])[O:5][CH2:6][CH:7]([OH:18])[CH2:8][CH2:9][O:10][Si:11]([CH3:17])([CH3:16])[C:12]([CH3:15])([CH3:14])[CH3:13])[CH3:3].C(N(CC)CC)C.[CH3:29][S:30](Cl)(=[O:32])=[O:31]>ClCCl>[CH3:29][S:30]([O:18][CH:7]([CH2:8][CH2:9][O:10][Si:11]([CH3:17])([CH3:16])[C:12]([CH3:13])([CH3:14])[CH3:15])[CH2:6][O:5][Si:4]([CH3:20])([CH3:19])[C:2]([CH3:21])([CH3:1])[CH3:3])(=[O:32])=[O:31]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 11416377HCID 11416377, compound2×

Product 1

HCID 86674468HCID 86674468, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2,2,3,3,10,10,11,11-octamethyl-4,9-dioxa-3,10-disiladodecan-6-ol (i.e. the product of Step A) (36.31 g, 0.109 mol) in dichloromethane (300 mL) cooled to about 0° C. under nitrogen, was added triethylamine (22.8 mL, 0.163 mol), followed by dropwise addition of a solution of methanesulfonyl chloride (10.14 mL, 0.13 mol) in dichloromethane (100 mL), maintaining the reaction mixture below 10° C. The reaction mixture was stirred for another 30 minutes, and then washed with citric acid (about 200 mL, 10%), water (about 200 mL) and sodium bicarbonate (about 200 mL), dried over magnesium sulfate, filtered and concentrated under reduced pressure to provide the title compound as a yellow oil (42.16 g) which was used without further purification.

Workup

  1. temperaturemaintaining the reaction mixture below 10° C
  2. washwashed with citric acid (about 200 mL, 10%), water (about 200 mL) and sodium bicarbonate (about 200 mL)
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a84cccb1a7c64d298fba142b61764561
Source dataset
uspto-grants-2014_09
Patent number
US08835427B2

Reaction notes

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