Sodium Chloride → 1-(4-Octylphenoxy)-3-(pyrrol-1-yl)propan-2-ol

HRID 1821917Notes

Reaction equation

HRID 1821917 reaction equation
[H-].[Na+].[NH:3]1[CH:7]=[CH:6][CH:5]=[CH:4]1.[CH2:8]([C:16]1[CH:26]=[CH:25][C:19]([O:20][CH2:21][CH:22]2[CH2:24][O:23]2)=[CH:18][CH:17]=1)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15].[Na+].[Cl-]>CN(C=O)C>[CH2:8]([C:16]1[CH:17]=[CH:18][C:19]([O:20][CH2:21][CH:22]([OH:23])[CH2:24][N:3]2[CH:7]=[CH:6][CH:5]=[CH:4]2)=[CH:25][CH:26]=1)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15]

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 8027PyrroleHCID 24758Sodium hydrideHCID 107248((p-Octylphenoxy)methyl)oxirane

Product 1

HCID 129928891-(4-Octylphenoxy)-3-(pyrrol-1-yl)propan-2-ol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

0.048 g (1.200 mmol) sodium hydride as 60% dispersion in mineral oil is suspended in 10 ml absolute DMF, stirred at room temperature for 10 min and admixed with 0.077 g (1.15 mmol) pyrrole. Having stirred for one hour, a solution of 0.300 g (1.14 mmol) 2-(4-octylphenoxymethyl)oxirane (Kuliev et al. Uch. Zap. Azerb. Gos. Univ. Ser. Khim Nauk. 1964, 4, 97; Chem. Abstr. 1966, 65, 640c) in 10 ml absolute DMF is added drop-wise. The mixture is stirred for 19 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 a red 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 yellowish oil.

Workup

  1. stirringHaving stirred for one hour
  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 a red 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-977afc4717cd4a35b76f1958bf6bcd36
Source dataset
uspto-grants-2009_10
Patent number
US07608633B2

Reaction notes

Loading…