Hydrogen Peroxide → HCID 18637141, compound

HRID 329528Notes

Reaction equation

HRID 329528 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH:8]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][O:24][CH:25]1[CH2:30][CH2:29][CH2:28][CH2:27][O:26]1)[CH2:9][O:10][CH2:11][C:12]1[O:17][CH2:16][CH2:15][CH2:14][CH:13]=1.[OH-:31].[Na+].OO>O1CCCC1.O>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH:8]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][O:24][CH:25]1[CH2:30][CH2:29][CH2:28][CH2:27][O:26]1)[CH2:9][O:10][CH2:11][C@H:12]1[C@H:13]([OH:31])[CH2:14][CH2:15][CH2:16][O:17]1

Participants

6

Reactant 3

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 15097265HCID 15097265, compound

Product 1

HCID 18637141HCID 18637141, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

1.46 ml of a 1M borane-tetrahydrofuran complex was added dropwise, whist ice-cooling, to a solution of 0.934 g of 6-[2,8-bis(tetrahydropyran-2-yloxy)octyloxymethyl]-3,4-dihydro-2H-pyran (prepared as described in Preparation 73) in 3 ml of tetrahydrofuran. The mixture was then stirred at room temperature for 4.5 hours. At the end of this time, 0.80 ml of a 10% w/v aqueous solution of sodium hydroxide and 0.60 ml of a 30% v/v aqueous solution of hydrogen peroxide were added, in turn, to the mixture at 30° to 40° C., and then the mixture was stirred at room temperature for a further 1 hour. The reaction mixture was then diluted with 50 ml of water and extracted twice with ethyl acetate. The combined extracts were washed with water, dried over anhydrous magnesium sulfate and concentrated by evaporation under reduced pressure, to give a residue, which was purified by column chromatography through 20 g of silica gel and by medium pressure liquid chromatography using a Lobar B column. 0.615 g of the title compound was obtained, as a colorless oil, from the fractions euted with a 7:3 by volume mixture of hexane and ethyl acetate.

Workup

  1. addition1.46 ml of a 1M borane-tetrahydrofuran complex was added dropwise
  2. stirringthe mixture was stirred at room temperature for a further 1 hour
  3. extractionextracted twice with ethyl acetate
  4. washThe combined extracts were washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated by evaporation under reduced pressure
  7. customto give a residue, which
  8. customwas purified by column chromatography through 20 g of silica gel and by medium pressure liquid chromatography

Sources & evidence

ORD record
ord-dcdb1612ae714160a128c36649afbc49
Source dataset
uspto-grants-1990_01
Patent number
US04891363

Reaction notes

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