Hydrochloric Acid → HCID 136335637, compound

HRID 1389560Notes

Reaction equation

HRID 1389560 reaction equation
[H-].[Na+].[CH3:3][SH:4].BrCCC([C:10]1[CH:15]=[C:14]([C:16]([CH3:19])([CH3:18])[CH3:17])[CH:13]=[CH:12][C:11]=1[OH:20])=O.Cl.O1C[CH2:25][CH2:24][CH2:23]1>CO>[CH3:23][CH2:24][CH2:25][C:3]([C:10]1[CH:15]=[C:14]([C:16]([CH3:17])([CH3:18])[CH3:19])[CH:13]=[CH:12][C:11]=1[OH:20])=[S:4]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 878MethanethiolHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 20297001HCID 20297001, compound

Product 1

HCID 136335637HCID 136335637, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a mixed solution of 1.65 g of sodium hydride (content 63%) and 15 ml of methanol were added 7.2 ml of 30% methylmercaptan in methanol and stirred at room temperature for 15 minutes. The solution was added dropwise to 4.289 g of 2-(3-bromopropionyl)-4-tert-butylphenol [described in Reference Example 3(h)] dissolved in 37.6 ml of tetrahydrofuran at room temperature and stirred at the same temperature for one hour. The reaction mixture was acidified with 1 N hydrochloric acid and extracted with ethyl acetate. The extract was washed with water, and saturated brine successively, dried over sodium sulfate anhydride and concentrated at reduced pressure. The residue was chromatographed on silica gel column using a mixed solvent of cyclohexane and ethyl acetate (30:1) as an eluting agent to give 2.304 g of the title compound of the following physical properties as pale yellow oil.

Workup

  1. stirringstirred at the same temperature for one hour
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water, and saturated brine successively
  4. dry with materialdried over sodium sulfate anhydride
  5. concentrationconcentrated at reduced pressure
  6. customThe residue was chromatographed on silica gel column

Sources & evidence

ORD record
ord-36e17b07e8664b379cee98f77091e148
Source dataset
uspto-grants-1981_01
Patent number
US04245099

Reaction notes

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