tert-Butyl mercaptan → Ethyl 4-(tert-butylthio)-3-oxobutanoate

HRID 1011557Notes

Reaction equation

HRID 1011557 reaction equation
Cl[CH2:2][C:3](=[O:10])[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].[CH3:11][C:12]([SH:15])([CH3:14])[CH3:13].C(N(CC)CC)C>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1COCC1>[CH2:8]([O:7][C:5](=[O:6])[CH2:4][C:3](=[O:10])[CH2:2][S:15][C:12]([CH3:14])([CH3:13])[CH3:11])[CH3:9]

Participants

6

Reactant 3

HCID 6387tert-Butyl mercaptanHCID 8471TriethylamineHCID 69484Ethyl 4-chloroacetoacetate

Product 1

HCID 10465978Ethyl 4-(tert-butylthio)-3-oxobutanoate

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 4-chloroacetoacetate (7.5 mL, 51.9 mmol), 2-methyl-2-propanethiol (5.6 mL, 49.7 mmol), triethylamine (10.8 mL, 77.4 mmol), and catalytic tetrabutylammonium bromide were dissolved in THF (250 mL) and stirred at room temperature overnight. Silica gel was added, and the mixture was concentrated and filtered over a plug of silica gel to obtain the desired product (B-1), which was used without further purification.

Workup

  1. additionSilica gel was added
  2. concentrationthe mixture was concentrated
  3. filtrationfiltered over a plug of silica gel

Sources & evidence

ORD record
ord-77b201fe09cb4019ab339a9649b15510
Source dataset
uspto-grants-2011_07
Patent number
US07977359B2

Reaction notes

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