Toluene → HCID 58078870, compound

HRID 929615Notes

Reaction equation

HRID 929615 reaction equation
[CH3:1][O:2][CH2:3][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][O:20][CH2:21][CH2:22][O:23][CH2:24][CH2:25][O:26][CH2:27][CH2:28][O:29][CH2:30][CH2:31][O:32][CH2:33][CH2:34][O:35][CH2:36][CH2:37][OH:38].[H-].[Na+].[CH2:41](Br)[C:42]#[CH:43].C1(C)C=CC=CC=1>CN(C=O)C>[CH3:1][O:2][CH2:3][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][O:20][CH2:21][CH2:22][O:23][CH2:24][CH2:25][O:26][CH2:27][CH2:28][O:29][CH2:30][CH2:31][O:32][CH2:33][CH2:34][O:35][CH2:36][CH2:37][O:38][CH2:41][C:42]#[CH:43]

Participants

6

Reactant 4

HCID 1140TolueneHCID 7842Propargyl bromideHCID 24758Sodium hydrideHCID 14550548HCID 14550548, compound

Product 1

HCID 58078870HCID 58078870, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

2,5,8,11,14,17,20,23,26,29,32,35-dodecaoxaheptatriacontan-37-ol (150 mg, 22.89 mmol, 1.0 equiv.) was slowly added to a slurry of NaH (48 mg, 45.78 mol, 8 equiv.) in DMF (1.4 mL) in a flame dried flask pre-cooled to 0° C. 80% propargyl bromide in toluene (36 □L, 27.47 mmol, 1.2 equiv.), cooled to 0° C., was added slowly. The ice bath was removed and the reaction was allowed to stir at room temperature for an additional 2 hours. The reaction was then re-cooled to 0° C., 0.5 mL of ice cold water was added, and the reaction was concentrated under reduced pressure. The remaining residue was redissolved in dichloromethane, then partially purified via silica gel chromatography (10% MeOH in DCM) to remove all the salts. After partial purification, 2,5,8,11,14,17,20,23,26,29,32,35,38-tridecaoxahentetracont-40-yne (s-13e) was obtained as a brown oil that was taken on to the next step without full purification.

Workup

  1. customdried flask
  2. additionwas added slowly
  3. customThe ice bath was removed
  4. temperatureThe reaction was then re-cooled to 0° C.
  5. addition0.5 mL of ice cold water was added
  6. concentrationthe reaction was concentrated under reduced pressure
  7. dissolutionThe remaining residue was redissolved in dichloromethane
  8. custompartially purified via silica gel chromatography (10% MeOH in DCM)
  9. customto remove all the salts
  10. customAfter partial purification

Sources & evidence

ORD record
ord-71bb3ddc133e4f3593fe14ddd29bd58e
Source dataset
uspto-grants-2016_03
Patent number
US09296708B2

Reaction notes

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