1H-Indole-3-carboxylic acid, 1,1-dimethylethyl ester → tert-Butyl-1-[2-acetoxy-3-(4-octylphenoxy)propyl]indole-3-carboxylate

HRID 1821941Notes

Reaction equation

HRID 1821941 reaction equation
[C:1]([O:5][C:6]([C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:10][CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].BrC[CH:19]([CH2:36]C([O-])=O)[CH2:20][O:21][C:22]1[CH:27]=[CH:26][C:25]([CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])=[CH:24][CH:23]=1>CS(C)=O.[Na+].[Cl-]>[C:1]([O:5][C:6]([C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]([CH2:36][CH:19]([O:7][C:6](=[O:5])[CH3:8])[CH2:20][O:21][C:22]2[CH:23]=[CH:24][C:25]([CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])=[CH:26][CH:27]=2)[CH:9]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 123081731H-Indole-3-carboxylic acid, 1,1-dimethylethyl esterHCID 86606004HCID 86606004, compound

Product 1

HCID 12992903tert-Butyl-1-[2-acetoxy-3-(4-octylphenoxy)propyl]indole-3-carboxylate

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 5234Sodium ChlorideSolvent

Conditions

Temperature
110 °C

Procedure

0.50 g (2.30 mmol) tert-butylindole-3-carboxylate is dissolved in 15 ml absolute DMSO, mixed with 0.28 g (2.50 mmol) potassium-tert-butylate and stirred at 110° C. for 15 min. A solution of 0.89 g (2.31 mmol) [1-bromo-3-(4-octylphenoxy)propan-2-yl]acetate in 15 ml absolute DMSO is added drop-wise. Following heating at 110° C. for 30 minutes and subsequent cooling, hydrolysis is carried out in 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 95:5) and yields the product as a yellowish oil.

Workup

  1. temperatureFollowing heating at 110° C. for 30 minutes
  2. customsubsequent cooling, hydrolysis
  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 with saturated NaCl solution
  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 flash column chromatography (flow agent: petroleum ether/ethyl acetate 95:5)

Sources & evidence

ORD record
ord-366aba25aaa8444c9c5b864326297070
Source dataset
uspto-grants-2009_10
Patent number
US07608633B2

Reaction notes

Loading…