Water → 3-Dodecyloxy-2-decyloxy-1-triphenylmethoxypropane

HRID 720815Notes

Reaction equation

HRID 720815 reaction equation
[C:1]([O:20][C:21]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[H-].[Na+].Br[CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH3:52].[OH2:53].[CH2:54]([O:56][CH2:57][CH3:58])[CH3:55]>O1CCCC1>[CH2:54]([O:56][CH2:57][CH:58]([O:53][CH2:24][CH2:23][CH2:22][CH2:21][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[CH2:1][O:20][C:21]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)([C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1)[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[CH2:55][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH3:52]

Participants

7

Reactant 5

HCID 962WaterHCID 3283Diethyl EtherHCID 81731-BromodecaneHCID 24758Sodium hydrideHCID 12756307Trityl ether

Product 1

HCID 218731963-Dodecyloxy-2-decyloxy-1-triphenylmethoxypropaneYield 52%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The trityl ether of Section B (13.5 g, 0.027 mol) was added dropwise to an ice-cooled suspension of sodium hydride (80%, 1.6 g, 0.054 mol) in 150 mL of tetrahydrofuran under nitrogen. After stirring for 2 hours at room temperature, heat was applied (55° C.). 1-Bromodecane (6 g, 0.027 mol) was added dropwise; heating was continued for 6 hours. After cooling for 3 hours, water was added slowly. Diethyl ether (2×100 mL) was added, and the solution washed with 15 percent sodium thiosulfite, water, and brine. After drying over sodium sulfate, the ether was removed, and the residue was chromatographed with a gradient of hexanes:ethyl acetate (100:0 to 20:1) to give 9 g (52%) of a clear liquid.

Workup

  1. temperaturecooled
  2. temperatureheat
  3. custom(55° C.)
  4. temperatureheating
  5. waitwas continued for 6 hours
  6. temperatureAfter cooling for 3 hours
  7. washthe solution washed with 15 percent sodium thiosulfite, water, and brine
  8. dry with materialAfter drying over sodium sulfate
  9. customthe ether was removed
  10. customthe residue was chromatographed with a gradient of hexanes:ethyl acetate (100:0 to 20:1)

Sources & evidence

ORD record
ord-8604ef8cdd9e46b0ad47118d1ed16547
Source dataset
uspto-grants-2006_11
Patent number
US07135584B2

Reaction notes

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