Sodium Bicarbonate → HCID 86749313, compound

HRID 1439953Notes

Reaction equation

HRID 1439953 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:14]=[C:15](S(C)=O)SC)[C:5]2[O:9][CH:8]3[CH2:10][CH:11]=[CH:12][CH:7]3[C:6]=2[CH:13]=1.Cl.C[OH:23].[C:24](=O)([O-])[OH:25].[Na+]>CO>[CH3:24][O:25][C:15](=[O:23])[CH2:14][C:4]1[C:5]2[O:9][CH:8]3[CH2:10][CH:11]=[CH:12][CH:7]3[C:6]=2[CH:13]=[C:2]([Br:1])[CH:3]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 21893726Hydrochloride methanolHCID 86749314HCID 86749314, compound

Product 1

HCID 86749313HCID 86749313, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(3aSR, 8bSR)-7-bromo-3a,8b-dihydro-5-(2-methylsulfinyl-2-methylthioethenyl)-3H-cyclopenta[b]benzofuran (5) (14.6 g) was dissolved in methanol (400 ml) followed by addition of a 5.24 N methanol hydrochloric acid solution (56 ml) while cooling with ice and stirring for 2 hours. Saturated sodium hydrogencarbonate solution was added to the reaction solution to neutralize followed by concentration. After extracting the residue with ethyl acetate (300 ml×2) and washing with water (50 ml) and brine (50 ml), it was dried with anhydrous magnesium sulfate and concentrated. The residue was then purified with column chromatography (silica gel: ethyl acetate/cyclohexane 1/20) to obtain the target compound (12.1 g, 99%).

Workup

  1. temperaturewhile cooling with ice
  2. concentrationto neutralize followed by concentration
  3. extractionAfter extracting the residue with ethyl acetate (300 ml×2)
  4. washwashing with water (50 ml) and brine (50 ml), it
  5. dry with materialwas dried with anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue was then purified with column chromatography (silica gel: ethyl acetate/cyclohexane 1/20)

Sources & evidence

ORD record
ord-cc20f684a82245eeb04f65721fc295ca
Source dataset
uspto-grants-1996_03
Patent number
US05496849

Reaction notes

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