Triethylamine → [(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl methanesulfonate

HRID 2353506Notes

Reaction equation

HRID 2353506 reaction equation
[CH3:1][C:2]1([CH3:9])[O:6][C@H:5]([CH2:7][OH:8])[CH2:4][O:3]1.C(N(CC)CC)C.[CH3:17][S:18](Cl)(=[O:20])=[O:19]>C1COCC1>[CH3:17][S:18]([O:8][CH2:7][C@@H:5]1[CH2:4][O:3][C:2]([CH3:9])([CH3:1])[O:6]1)(=[O:20])=[O:19]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 736056(R)-Solketal

Product 1

HCID 24903512[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The (R)-(−)-2,2-dimethyl-1,3-dioxolane-4-methanol (Aldrich, 0.38 mL, 3.1 mmol), triethylamine (0.85 mL, 6.1 mmol), and methanesulfonyl chloride (0.31 mL, 4.1 mmol) in 10 mL THF were processed as described in Example 1C to give the title compound that was used directly in the next reaction.

Sources & evidence

ORD record
ord-7d7bbc71a32349d78c83d27840896f6b
Source dataset
uspto-grants-2010_07
Patent number
US07750039B2

Reaction notes

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