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

HRID 1821938Notes

Reaction equation

HRID 1821938 reaction equation
C(OC(=O)C)(=O)C.[C:8]([O:12][C:13]([C:15]1[N:16]([CH2:24][CH:25]([OH:42])[CH2:26][O:27][C:28]2[CH:33]=[CH:32][C:31]([CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])=[CH:30][CH:29]=2)[C:17]2[C:22]([CH:23]=1)=[CH:21][CH:20]=[CH:19][CH:18]=2)=[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[N:16]([CH2:24][C:25](=[O:42])[CH2:26][O:27][C:28]2[CH:33]=[CH:32][C:31]([CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])=[CH:30][CH:29]=2)[C:17]2[C:22]([CH:23]=1)=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:14])([CH3:11])([CH3:10])[CH3:9]

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 11627108tert-Butyl-1-[2-hydroxy-3-(4-octylphenoxy)propyl]indole-2-carboxylate

Product 1

HCID 11670138tert-Butyl-1-[3-(4-octylphenoxy)-2-oxopropyl]indole-2-carboxylate

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

1.02 g (10.0 mmol) acetic anhydride are mixed with 10 ml absolute DMSO, stirred at room temperature for 10 min and added drop-wise to a solution of 0.120 g (0.250 mmol) tert-butyl-1-[2-hydroxy-3-(4-octylphenoxy)propyl]indole-2-carboxylate in 10 ml absolute DMSO. Having stirred for 8 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 with diethyl ether, combination of the organic phases, concentration to half the volume on the rotary evaporator, three wash steps using saturated NaCl solution, drying on sodium sulfate, filtration and reconcentration on the rotary evaporator leave as a crude product a yellow oil which is purified on silica gel by means of column chromatography (flow agent: petroleum ether/ethyl acetate 98:2) and yields the product as a yellowish oil.

Workup

  1. stirringHaving stirred for 8 hours
  2. waitv/v) and hydrolyzed for 10 min
  3. extractionFour extractions
  4. concentrationwith diethyl ether, combination of the organic phases, concentration to half the volume
  5. customon the rotary evaporator, three
  6. washwash steps
  7. customdrying on sodium sulfate, filtration and reconcentration on the rotary evaporator
  8. customleave as a crude product a yellow oil which
  9. customis purified on silica gel by means of column chromatography (flow agent: petroleum ether/ethyl acetate 98:2)

Sources & evidence

ORD record
ord-e032db312e104bb3ad27da34b498db32
Source dataset
uspto-grants-2009_10
Patent number
US07608633B2

Reaction notes

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