Sodium Chloride → tert-Butyl-1-[3-(4-octylphenoxy)-2-oxopropyl]pyrrole-3-carboxylate

HRID 1821933Notes

Reaction equation

HRID 1821933 reaction equation
C(OC(=O)C)(=O)C.[C:8]([O:12][C:13]([C:15]1[CH:19]=[CH:18][N:17]([CH2:20][CH:21]([OH:38])[CH2:22][O:23][C:24]2[CH:29]=[CH:28][C:27]([CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])=[CH:26][CH:25]=2)[CH:16]=1)=[O:14])([CH3:11])([CH3:10])[CH3:9].C(=O)([O-])O.[Na+].[Na+].[Cl-]>CS(C)=O>[C:8]([O:12][C:13]([C:15]1[CH:19]=[CH:18][N:17]([CH2:20][C:21](=[O:38])[CH2:22][O:23][C:24]2[CH:29]=[CH:28][C:27]([CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])=[CH:26][CH:25]=2)[CH:16]=1)=[O:14])([CH3:11])([CH3:10])[CH3:9]

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 12992900tert-Butyl-1-[2-hydroxy-3-(4-octylphenoxy)propyl]pyrrole-3-carboxylate

Product 1

HCID 12992901tert-Butyl-1-[3-(4-octylphenoxy)-2-oxopropyl]pyrrole-3-carboxylate

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

0.817 g (8.00 mmol) acetic anhydride is mixed with 10 ml absolute DMSO, stirred at room temperature for 10 min and added drop-wise to a solution of 0.086 g (0.200 mmol) tert-butyl-1-[2-hydroxy-3-(4-octylphenoxy)propyl]pyrrole-3-carboxylate in 10 ml absolute DMSO. Having stirred for 19 hours, the solution is poured into a mixture of 5% sodium hydrogen carbonate solution and saturated NaCl solution (1:1, v/v) and hydrolyzed for 10 min. Four extractions using diethyl ether, combination of the organic phases, concentration to half the volume on the rotary evaporator, three wash steps with saturated NaCl solution, drying on sodium sulfate, filtration and reconcentration on the rotary evaporator leave as a crude product a brown oil which is purified on silica gel by means of flash column chromatography (flow agent: petroleum ether/ethyl acetate 90:10) and yields the product as a yellowish oil.

Workup

  1. stirringHaving stirred for 19 hours
  2. waitv/v) and hydrolyzed for 10 min
  3. extractionFour extractions
  4. concentrationdiethyl ether, combination of the organic phases, concentration to half the volume
  5. customon the rotary evaporator, three
  6. washwash steps with saturated NaCl solution
  7. customdrying on sodium sulfate, filtration and reconcentration on the rotary evaporator
  8. customleave as a crude product a brown oil which
  9. customis purified on silica gel by means of flash column chromatography (flow agent: petroleum ether/ethyl acetate 90:10)

Sources & evidence

ORD record
ord-6bb63cff3bb84a24a4a231ee84f2edca
Source dataset
uspto-grants-2009_10
Patent number
US07608633B2

Reaction notes

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