Triethylamine → HCID 10503096, compound

HRID 355549Notes

Reaction equation

HRID 355549 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[S:7][C:8]([CH2:11][CH2:12][C@H:13]([OH:23])[CH2:14][O:15][Si:16]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17])=[CH:9][CH:10]=1)=[O:5])[CH3:2].C(N(CC)CC)C.[CH3:31][S:32](Cl)(=[O:34])=[O:33]>C(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[S:7][C:8]([CH2:11][CH2:12][C@H:13]([O:23][S:32]([CH3:31])(=[O:34])=[O:33])[CH2:14][O:15][Si:16]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:17])[CH3:18])=[CH:9][CH:10]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 10808359HCID 10808359, compound

Product 1

HCID 10503096HCID 10503096, compoundYield 94.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred, ice-cold solution of 23.19 g (64.68 mmol) of the alcohol (16) and 13.5 ml (96.86 mmol) of triethylamine in 200 ml of CH2Cl2 was added 6.0 ml (77.52 mmol) of methanesulfonyl chloride. After 30 minutes at 0° C., the reaction mixture was warmed to room temperature. After another 30 minutes, the reaction mixture was diluted with CH2Cl2 and then washed sequentially with 0.5N HCl, saturated NaHCO3 and saturated NaCl. The organic layer was dried (MgSO4) and the solvent was removed under reduced pressure, yielding 26.61 g (94%) of the desired mesylate (17) as a colorless oil, which was used in the next step without further purification.

Workup

  1. waitAfter another 30 minutes
  2. washwashed sequentially with 0.5N HCl, saturated NaHCO3 and saturated NaCl
  3. dry with materialThe organic layer was dried (MgSO4)
  4. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-4ad7509896d844b2a9ea2af72633fba8
Source dataset
uspto-grants-1998_11
Patent number
US05831100

Reaction notes

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