1-Bromododecane → HCID 67397584, compound

HRID 2407914Notes

Reaction equation

HRID 2407914 reaction equation
[CH2:1]([O:8][CH2:9][C@H:10]([OH:13])[CH2:11][OH:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26].[OH-].[K+]>C1COCC1.C(OCC)C>[CH2:15]([O:13][C@H:10]([CH2:11][O:12][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH3:15])[CH2:9][O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]

Participants

6

Reactant 3

HCID 89191-BromododecaneHCID 14797Potassium HydroxideHCID 2724795(R)-3-(benzyloxy)propane-1,2-diol

Product 1

HCID 67397584HCID 67397584, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (R)-3-(benzyloxy)propane-1,2-diol (1 eq) in THF (0.3 M) was added n-tetrabutylammonium bromide (0.2 eq), 1-bromododecane (4 eq) and potassium hydroxide (5 eq). The reaction mixture was stirred at room temperature overnight. The mixture was diluted with ethyl ether, washed with water, 1 N hydrochloric acid, water, and brine, dried over anhydrous Na2SO4, and concentrated en vaccuo. The crude mixture was purified by flash chromatography on a COMBIFLASH® system (ISCO) using 0-10% EtOAc/Hex to give the product.

Workup

  1. washwashed with water, 1 N hydrochloric acid, water, and brine
  2. dry with materialdried over anhydrous Na2SO4
  3. concentrationconcentrated en vaccuo
  4. customThe crude mixture was purified by flash chromatography on a COMBIFLASH® system (ISCO)
  5. customto give the product

Sources & evidence

ORD record
ord-d7375df1ca5b43fe8ec0eed96c1c53f6
Source dataset
uspto-grants-2014_08
Patent number
US08808703B2

Reaction notes

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