Hydrochloric Acid → HCID 22036226, compound

HRID 2075727Notes

Reaction equation

HRID 2075727 reaction equation
Br[C:2]1[CH:3]=[C:4]([SH:8])[CH:5]=[CH:6][CH:7]=1.[H-].[Na+].C([Li])CCC.[CH3:16][CH2:17][C:18](=[O:21])[CH2:19][CH3:20].Cl>C1COCC1>[SH:8][C:4]1[CH:3]=[C:2]([C:18]([OH:21])([CH2:19][CH3:20])[CH2:17][CH3:16])[CH:7]=[CH:6][CH:5]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 7288Ethyl ketoneHCID 24758Sodium hydrideHCID 80597m-BromobenzenethiolHCID 178418339Butyllithium

Product 1

HCID 22036226HCID 22036226, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To 3-Bromobenzenethiol (1.6 mL, 13.5 mmol) in THF (10 mL) at 0° C. was added sodium hydride (60 wt %, 600 mg, 14.9 mmol). After stirring for 10 minutes, the reaction was cooled to −78° C. and n-butyllithium (7.4 mL, 14.9 mmol) was added dropwise. After stirring for 20 minutes, 3-pentanone (1.6 mL, 14.9 mmol) was added, and the reaction was slowly warmed to room temperature and immediately acidified with 1N aqueous HCl to pH 3. The reaction mixture was extracted with EtOAc, and the combined organic layers were dried over MgSO4, filtered, and concentrated. The residue was purified by silica gel chromatography (5% EtOAc in hexanes) to give the desired product, 10l.

Workup

  1. stirringAfter stirring for 20 minutes
  2. temperaturethe reaction was slowly warmed to room temperature
  3. extractionThe reaction mixture was extracted with EtOAc
  4. dry with materialthe combined organic layers were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography (5% EtOAc in hexanes)

Sources & evidence

ORD record
ord-eaa01b47ea65419fad376d726a5f4a6e
Source dataset
uspto-grants-2011_04
Patent number
US07919621B2

Reaction notes

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