Indole → 1-(Indol-1-yl)-3-(4-octylphenoxy)propan-2-ol

HRID 1821921Notes

Reaction equation

HRID 1821921 reaction equation
[H-].[Na+].[NH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4]1.[CH2:12]([C:20]1[CH:30]=[CH:29][C:23]([O:24][CH2:25][CH:26]2[CH2:28][O:27]2)=[CH:22][CH:21]=1)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19].[Na+].[Cl-]>CN(C=O)C>[N:3]1([CH2:28][CH:26]([OH:27])[CH2:25][O:24][C:23]2[CH:29]=[CH:30][C:20]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])=[CH:21][CH:22]=2)[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4]1

Participants

6

Reactant 4

HCID 798IndoleHCID 5234Sodium ChlorideHCID 24758Sodium hydrideHCID 107248((p-Octylphenoxy)methyl)oxirane

Product 1

HCID 129928921-(Indol-1-yl)-3-(4-octylphenoxy)propan-2-ol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

0.048 g (1.20 mmol) sodium hydride as 60% dispersion in mineral oil are suspended in 10 ml absolute DMF, stirred at room temperature for 10 min and mixed with a solution of 0.134 g (1.14 mmol) indole in 10 ml absolute DMF. Having stirred for 1½ hours, a solution of 0.300 g (1.14 mmol) 2-(4-octylphenoxymethyl)oxirane in 10 ml absolute DMF is added drop-wise. The mixture is stirred for 16 hours, hydrolyzed with a semi-saturated NaCl solution and extracted four times using diethyl ether. The combined organic phases are concentrated to half the volume on the rotary evaporator and washed three times with saturated NaCl solution. Drying on sodium sulfate, filtration and reconcentration on the rotary evaporator leave as a crude product an orange oil which is purified on silica gel by means of column chromatography (flow agent: petroleum ether/ethyl acetate 95:5) and yields the product as a yellow oil.

Workup

  1. stirringHaving stirred for 1½ hours
  2. extractionextracted four times
  3. concentrationThe combined organic phases are concentrated to half the volume
  4. customon the rotary evaporator
  5. washwashed three times with saturated NaCl solution
  6. customDrying on sodium sulfate, filtration and reconcentration on the rotary evaporator
  7. customleave as a crude product an orange oil which
  8. customis purified on silica gel by means of column chromatography (flow agent: petroleum ether/ethyl acetate 95:5)

Sources & evidence

ORD record
ord-59b85329321047b4b24b912d738a7e21
Source dataset
uspto-grants-2009_10
Patent number
US07608633B2

Reaction notes

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