Triethylamine → Butanoic acid, 2,2-dimethyl-4-[(methylsulfonyl)oxy]-, methyl ester

HRID 1798460Notes

Reaction equation

HRID 1798460 reaction equation
[OH:1][CH2:2][CH2:3][C:4]([CH3:10])([CH3:9])[C:5]([O:7][CH3:8])=[O:6].[CH3:11][S:12](Cl)(=[O:14])=[O:13].C(N(CC)CC)C>C(Cl)Cl>[CH3:9][C:4]([CH3:10])([CH2:3][CH2:2][O:1][S:12]([CH3:11])(=[O:14])=[O:13])[C:5]([O:7][CH3:8])=[O:6]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 18942524HCID 18942524, compound

Product 1

HCID 59323533Butanoic acid, 2,2-dimethyl-4-[(methylsulfonyl)oxy]-, methyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-20 °C

Procedure

To a solution of methyl 4-hydroxy-2,2-dimethylbutanoate (1 eq.) from the previous step in DCM (0.1 M) at −40° C. was added methanesulfonyl chloride (1.5 eq.) and triethylamine (3.0 eq.). The reaction was warmed to −20° C. over 30 min and then quenched with saturated aqueous NaHCO3 solution. The aqueous phase was extracted with DCM. The combined organic extracts were dried over MgSO4 and concentrated in vacuo. The crude product was used in the next step without further purification.

Workup

  1. customquenched with saturated aqueous NaHCO3 solution
  2. extractionThe aqueous phase was extracted with DCM
  3. dry with materialThe combined organic extracts were dried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe crude product was used in the next step without further purification

Sources & evidence

ORD record
ord-6774bc24ea1542419a9b9a7aa56594c7
Source dataset
uspto-grants-2013_01
Patent number
US08343968B2

Reaction notes

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