tert-Butyl mercaptan → Ethyl 5-(tert-butylsulfanyl)-2,2-dimethyl-4-oxopentanoate

HRID 1620804Notes

Reaction equation

HRID 1620804 reaction equation
O1CCCC1.[CH2:6]([O:8][C:9](=[O:18])[C:10]([CH3:17])([CH3:16])[CH2:11][C:12](=[O:15])[CH2:13]Br)[CH3:7].[CH3:19][C:20]([SH:23])([CH3:22])[CH3:21].C(N(CC)CC)C>CCCCCC>[CH2:6]([O:8][C:9](=[O:18])[C:10]([CH3:17])([CH3:16])[CH2:11][C:12](=[O:15])[CH2:13][S:23][C:20]([CH3:22])([CH3:21])[CH3:19])[CH3:7]

Participants

6

Reactant 4

HCID 6387tert-Butyl mercaptanHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 4090969Ethyl 5-bromo-2,2-dimethyl-4-oxopentanoate

Product 1

HCID 3576811Ethyl 5-(tert-butylsulfanyl)-2,2-dimethyl-4-oxopentanoate

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
-2.5 °C

Procedure

To a reaction flask containing tetrahydrofuran (5.0-fold, V/W of starting material) was added 5-bromo-2,2-dimethyl-4-oxo-pentanoic acid ethyl ester (1.0 eq) under nitrogen. The mixture was cooled to a temperature of −5-0° C., and a solution of 2-methyl-2-propanethiol (1.2 eq) and triethylamine (1.25 eq) was added while maintaining the temperature below 0° C. The reaction was stirred at room temperature for 25 hours, and then hexane (3.0-fold, V/W of starting material) was slowly added. After agitating for 30 minutes, the solid material was removed by filtration and washed with 50% ethyl acetate/hexane solution. The filtrate was concentrated under reduced pressure to give the desired product, which was taken on to the next step without further purification.

Workup

  1. temperaturewhile maintaining the temperature below 0° C
  2. stirringAfter agitating for 30 minutes
  3. customthe solid material was removed by filtration
  4. washwashed with 50% ethyl acetate/hexane solution
  5. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-3f005074dc9648be948a40463512051c
Source dataset
uspto-grants-2014_07
Patent number
US08772495B2

Reaction notes

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