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Hydrogen Peroxide → HCID 23372103, compound

HRID 1975562
Notes
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Reaction equation

HRID 1975562 reaction equation
[CH2:1]([O:4][CH:5]1[CH2:10][C:9]([CH3:12])([CH3:11])[N:8]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[C:7]([CH3:23])([CH3:22])[CH2:6]1)[CH:2]=[CH2:3].C12BC(CCC1)CCC2.[OH-:33].[Na+].OO>O1CCCC1.O.CCOCC>[CH2:14]([O:13][N:8]1[C:7]([CH3:22])([CH3:23])[CH2:6][CH:5]([O:4][CH2:1][CH2:2][CH2:3][OH:33])[CH2:10][C:9]1([CH3:11])[CH3:12])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 789669-Borabicyclo(3.3.1)nonaneHCID 233721064-Allyloxy-1-octyloxy-2,2,6,6-tetramethylpiperidine

Product 1

HCID 23372103HCID 23372103, compoundYield 89%

Reagents, catalysts & solvents 3

HCID 962
Water
Solvent
HCID 3283Diethyl EtherSolvent
HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
20 °C

Procedure

A solution of 14.9 grams (45.9 mmol) of 4-allyloxy-1-octyloxy-2,2,6,6-tetramethylpiperidine (prepared in Example 10A) in 20 ml of anhydrous tetrahydrofuran is added over a 10-minute period to a solution of 5.6 grams (45.9 mmol) of 9-borabicyclo [3.3.1]nonane in 20 ml of tetrahydrofuran under a nitrogen atmosphere. The reaction mixture is cooled to 20° C., and a solution of 1.84 gram (45.9 mmol) of sodium hydroxide in water is added over a 10-minute period. A solution of 15.3 ml of 30% aqueous hydrogen peroxide is then added over 30 minutes while the reaction mixture is cooled in an ice-water bath. The reaction mixture is diluted with ether (50 ml) and the organic layer is separated and dried over potassium carbonate. Solvent is evaporated and the residue is purified by flash chromatography (silica gel; 2:1 heptane:ethyl acetate) to afford 14.0 grams (89 % yield) of the title compound is a colorless syrup.

Workup

  1. temperatureis cooled in an ice-water bath
  2. customthe organic layer is separated
  3. dry with materialdried over potassium carbonate
  4. customSolvent is evaporated
  5. customthe residue is purified by flash chromatography (silica gel; 2:1 heptane:ethyl acetate)

Sources & evidence

ORD record
ord-ed3dd35e56dc4fe683c02da7f002ef5c
Source dataset
uspto-grants-1994_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05286865

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes