Toluene → HCID 44475517, compound

HRID 2088261Notes

Reaction equation

HRID 2088261 reaction equation
[H-].[Na+].[CH2:3]([OH:21])[CH2:4][O:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][O:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19][OH:20].[CH2:22](Br)[C:23]#[CH:24].C1(C)C=CC=CC=1>C1COCC1>[CH2:19]([OH:20])[CH2:18][O:17][CH2:16][CH2:15][O:14][CH2:13][CH2:12][O:11][CH2:10][CH2:9][O:8][CH2:7][CH2:6][O:5][CH2:4][CH2:3][O:21][CH2:24][C:23]#[CH:22]

Participants

6

Reactant 4

HCID 1140TolueneHCID 7842Propargyl bromideHCID 17472Hexaethylene GlycolHCID 24758Sodium hydride

Product 1

HCID 44475517HCID 44475517, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Sodium hydride, 60% dispersion in mineral oil, (0.86 g, 21.4 mmol) was added in portions to the solution of hexaethylene glycol (5.5 g, 19.4 mmol) in anhydrous THF (40 mL) at 0° C. (FIG. 3). The reaction mixture was stirred at 0° C. for 15 minutes then propargyl bromide, 80% in toluene, (2.4 mL, 21.4 mmol) was added dropwise. The mixture was allowed to warm to room temperature and stirred for 3 hours. The formed sodium bromide was removed by filtration and the solvent was evaporated. The crude product was purified on SiO2 column using methanol/dichloromethane gradient 0-100% to yield 3.4 g (54%) of 1 as a colorless oil. 1H NMR (500 MHz, CDCl3): δ 2.45 (t, J=2.4 Hz, 1H), 2.74 (bs, 1H), 3.61-3.71 (m, 24H), 4.21 (d, J=2.4 Hz, 2H); 13C NMR (100.6 MHz, CDCl3): δ 58.4, 61.7, 69.1, 70.3-70.6, 72.5, 74.5, 79.7; MS ESI (m/z): [M+H]+ calcd. for C15H29O7, 321.38; found 321.4.

Workup

  1. temperatureto warm to room temperature
  2. stirringstirred for 3 hours
  3. customThe formed sodium bromide was removed by filtration
  4. customthe solvent was evaporated
  5. customThe crude product was purified on SiO2 column

Sources & evidence

ORD record
ord-81b34f936ee4408a97f4d448afdbd57c
Source dataset
uspto-grants-2013_05
Patent number
US08435488B2

Reaction notes

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