Hydrochloric Acid → Dicyclopropyl-(3-mercapto-phenyl)-methanol

HRID 2075725Notes

Reaction equation

HRID 2075725 reaction equation
Br[C:2]1[CH:3]=[C:4]([SH:8])[CH:5]=[CH:6][CH:7]=1.[H-].[Na+].C([Li])CCC.[CH:16]1([C:19]([CH:21]2[CH2:23][CH2:22]2)=[O:20])[CH2:18][CH2:17]1.Cl>C1COCC1>[CH:16]1([C:19]([CH:21]2[CH2:23][CH2:22]2)([C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([SH:8])[CH:3]=2)[OH:20])[CH2:18][CH2:17]1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 70721Dicyclopropyl ketoneHCID 80597m-BromobenzenethiolHCID 178418339Butyllithium

Product 1

HCID 67090951Dicyclopropyl-(3-mercapto-phenyl)-methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-5 °C

Procedure

3-Bromobenzenethiol (2.0 g, 10.6 mmol) was dissolved in THF (20 mL) and cooled to −5° C. under N2. Sodium hydride (60 wt %, 477 mg, 11.6 mmol) was added portionwise, and the reaction was then cooled to −78° C. n-Butyllithium (2.5M, 4.7 mL, 11.6 mmol) was added over 20 minutes, followed by dicyclopropylmethanone (1.2 mL, 10.6 mmol), and the reaction was slowly warmed to room temperature over 3 hours. The reaction was acidified with 1N aqueous HCl to pH 2, and the reaction mixture was extracted with EtOAc three times. The combined organic layers were dried over MgSO4, filtered, and concentrated. The residue was purified by silica gel chromatography (0-80% EtOAc in hexanes) to give the desired product, 10i.

Workup

  1. additionwas added over 20 minutes
  2. temperaturethe reaction was slowly warmed to room temperature over 3 hours
  3. extractionthe reaction mixture was extracted with EtOAc three times
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography (0-80% EtOAc in hexanes)

Sources & evidence

ORD record
ord-3740511d712340d7801013f48c4a76f0
Source dataset
uspto-grants-2011_04
Patent number
US07919621B2

Reaction notes

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