Hydrogen Peroxide → HCID 22841027, compound

HRID 414771Notes

Reaction equation

HRID 414771 reaction equation
B.[CH2:2]([O:18][CH2:19][C:20]1[O:25][CH2:24][CH2:23][CH2:22][CH:21]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17].[OH-:26].[Na+].OO>O1CCCC1.O>[CH2:2]([O:18][CH2:19][C@H:20]1[C@H:21]([OH:26])[CH2:22][CH2:23][CH2:24][O:25]1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 6331BoraneHCID 14798Sodium HydroxideHCID 13982249HCID 13982249, compound

Product 1

HCID 22841027HCID 22841027, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

11 ml of a 1M tetrahydrofuran solution of borane was added dropwise, whilst ice-cooling, to a solution of 5.53 g of 6-hexadecyloxymethyl-3,4-dihydro-2H-pyran (prepared as described in Preparation 1) dissolved in 12 ml of tetrahydrofuran. The reaction mixture was stirred at room temperature for 3 hours, after which 4 ml of a 3N aqueous solution of sodium hydroxide were added to it, and then 4 ml of 30% hydrogen peroxide were added dropwise into it at 30°-40° C. The reaction mixture was then stirred at room temperature for 1 hour, after which it was poured in water. The mixture was then washed with a saturated aqueous solution of sodium chloride, and then the organic layer was separated, dried and condensed by evaporation under reduced pressure. The oily residue was subjected to column chromatography through 100 g of silica gel. The fraction eluted with mixtures of ethyl acetate and hexane ranging from 1:5 to 1:2 by volume gave 5.18 g of the title compound as crystals. Recrystallization from hexane gave needles, melting at 41.5°-43° C.

Workup

  1. stirringThe reaction mixture was then stirred at room temperature for 1 hour
  2. washThe mixture was then washed with a saturated aqueous solution of sodium chloride
  3. customthe organic layer was separated
  4. customdried
  5. customcondensed
  6. customby evaporation under reduced pressure
  7. washThe fraction eluted with mixtures of ethyl acetate and hexane ranging from 1:5 to 1:2 by volume

Sources & evidence

ORD record
ord-9021695c564b4cd79671bbfb314611e7
Source dataset
uspto-grants-1988_12
Patent number
US04794183

Reaction notes

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