Triethylamine → (2,2-Dimethyl-1,3-dioxan-5-yl)methyl methanesulfonate

HRID 339633Notes

Reaction equation

HRID 339633 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].CCN(CC)CC.[CH3:13][C:14]1([CH3:22])[O:19][CH2:18][CH:17]([CH2:20][OH:21])[CH2:16][O:15]1>C(Cl)Cl>[CH3:13][C:14]1([CH3:22])[O:19][CH2:18][CH:17]([CH2:20][O:21][S:2]([CH3:1])(=[O:4])=[O:3])[CH2:16][O:15]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 3584869(2,2-Dimethyl-1,3-dioxan-5-yl)methanol

Product 1

HCID 10998661(2,2-Dimethyl-1,3-dioxan-5-yl)methyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

MsCl (4.4 mL, 56 mmol) was added slowly to a solution of Et3N (9.8 mL, 71 mmol) and (2,2-dimethyl-[1,3]dioxan-5-yl)-methanol (6.87 g, 47.0 mmol) in CH2Cl2 (100 mL) at 0° C. (bath temp). The reaction mixture was stirred at rt for 2 h and then quenched with H2O (100 mL). The mixture was extracted with CH2Cl2 and the organic fractions were dried (MgSO4) and concentrated in vacuo to give the title compound as a colorless liquid: yield 10.02 g (95%).

Workup

  1. customquenched with H2O (100 mL)
  2. extractionThe mixture was extracted with CH2Cl2
  3. dry with materialthe organic fractions were dried (MgSO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5fa07e7b409549e9bb98556a7b2158d7
Source dataset
uspto-grants-2014_11
Patent number
US08895534B2

Reaction notes

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