Water → HCID 18765939, compound

HRID 480998Notes

Reaction equation

HRID 480998 reaction equation
[C:1]1([C:7]([NH:20][CH2:21][CH2:22][OH:23])([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[Cl:26][CH:27](Cl)[C:28]1[C:29]([CH3:34])=[CH:30][CH:31]=[CH:32][CH:33]=1.O>C1COCC1>[Cl:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[CH2:34][O:23][CH2:22][CH2:21][NH:20][C:7]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 587032Benzene, 1-(dichloromethyl)-2-methyl-HCID 31256082-((Triphenylmethyl)amino)ethanol

Product 1

HCID 18765939HCID 18765939, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2-(triphenylmethylamino)ethanol (5.00 g, 16.5 mmol) in THF (20 ml) was added dropwise to a suspension of NaH (60% in oil, 0.79 g, 19.8 mmol) in THF (30 ml) at room temperature and the mixture was stirred for 0.5 hour. α,α-Dichloro-o-xylene (1.56 g, 66.0 mmol) was added and the mixture was stirred for 24 h at reflux temperature. The mixture was poured into water (50 ml) and the whole was extracted with ether (50 ml×2). The combined organic layers were washed with brine, dried over magnesium sulfate, and concentrated in vacuo. The residue was purified by column chromatography on silica gel (hexane/ethyl acetate=15/1 as eluent) to afford the titled compound as a colorless oil. (1.00 g, 14%)

Workup

  1. stirringthe mixture was stirred for 24 h
  2. temperatureat reflux temperature
  3. extractionthe whole was extracted with ether (50 ml×2)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography on silica gel (hexane/ethyl acetate=15/1 as eluent)

Sources & evidence

ORD record
ord-4c50ddf508144e878fa26b12bd851d98
Source dataset
uspto-grants-2003_11
Patent number
US06653313B2

Reaction notes

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