Sodium Chloride → tert-Butyl-1-[2-hydroxy-3-(4-octylphenoxy)propyl]indole-5-carboxylate

HRID 1821946Notes

Reaction equation

HRID 1821946 reaction equation
[H-].[Na+].[C:3]([O:7][C:8]([C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[NH:15][CH:14]=[CH:13]2)=[O:9])([CH3:6])([CH3:5])[CH3:4].[CH2:19]([C:27]1[CH:37]=[CH:36][C:30]([O:31][CH2:32][CH:33]2[CH2:35][O:34]2)=[CH:29][CH:28]=1)[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26].[Na+].[Cl-]>CN(C=O)C>[C:3]([O:7][C:8]([C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[N:15]([CH2:35][CH:33]([OH:34])[CH2:32][O:31][C:30]1[CH:36]=[CH:37][C:27]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[CH:28][CH:29]=1)[CH:14]=[CH:13]2)=[O:9])([CH3:6])([CH3:4])[CH3:5]

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 24758Sodium hydrideHCID 107248((p-Octylphenoxy)methyl)oxiraneHCID 11183550Tert-butyl 1H-indole-5-carboxylate

Product 1

HCID 12992906tert-Butyl-1-[2-hydroxy-3-(4-octylphenoxy)propyl]indole-5-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

0.077 g (1.93 mmol) sodium hydride as a 60% dispersion in mineral oil is suspended in 15 ml absolute DMF, stirred at room temperature for 10 min, mixed with a solution of 0.400 g (1.84 mmol) tert-butylindole-5-carboxylate in 15 ml absolute DMF and stirred at room temperature for one hour. A solution of 0.483 g (1.84 mmol) 2-(4-octyl-phenoxymethyl)oxirane in 15 ml absolute DMF is added drop-wise. Following four hours of heating at 60° C. and subsequent cooling, hydrolysis is carried out in a semi-saturated NaCl solution. Four extractions with 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 yellow 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 colorless oil.

Workup

  1. stirringstirred at room temperature for one hour
  2. waitFollowing four hours
  3. temperatureof heating at 60° C.
  4. customsubsequent cooling, hydrolysis
  5. extractionFour extractions
  6. concentrationwith diethyl ether, combination of the organic phases, concentration to half the volume
  7. customon the rotary evaporator, three
  8. washwash steps with saturated NaCl solution
  9. customdrying on sodium sulfate, filtration and reconcentration on the rotary evaporator
  10. customleave as a crude product a yellow oil which
  11. customis purified on silica gel by means of flash column chromatography (flow agent: petroleum ether/ethyl acetate 90:10)

Sources & evidence

ORD record
ord-19fed8a7334e48a0809d7878534c250e
Source dataset
uspto-grants-2009_10
Patent number
US07608633B2

Reaction notes

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