Hydrogen Peroxide → HCID 70231396, compound

HRID 618494Notes

Reaction equation

HRID 618494 reaction equation
[C:1]12([C:11]3[CH:20]=[C:19]4[C:14]([CH:15]=[CH:16][C:17]([C:21]5[CH:30]=[CH:29][C:24]([C:25]([O:27][CH3:28])=[O:26])=[CH:23][CH:22]=5)=[CH:18]4)=[CH:13][C:12]=3[CH2:31][CH:32]=[CH2:33])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.C12BC(CCC1)CCC2.[OH-:43].[Na+].OO>O.C1COCC1>[C:1]12([C:11]3[CH:20]=[C:19]4[C:14]([CH:15]=[CH:16][C:17]([C:21]5[CH:22]=[CH:23][C:24]([C:25]([O:27][CH3:28])=[O:26])=[CH:29][CH:30]=5)=[CH:18]4)=[CH:13][C:12]=3[CH2:31][CH2:32][CH2:33][OH:43])[CH2:2][CH:3]3[CH2:4][CH:5]([CH2:6][CH:7]([CH2:9]3)[CH2:8]1)[CH2:10]2

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 789669-Borabicyclo(3.3.1)nonaneHCID 22000378HCID 22000378, compound

Product 1

HCID 70231396HCID 70231396, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

1.7 g (3.9 mmol) of methyl 4-[7-(1-adamantyl)-6-allyl-2-naphthyl]benzoate and 40 ml of THF were introduced into a round-bottomed flask under a stream of nitrogen. A solution of 23.5 ml (11.7 mmol) of 9-borabicyclo[3.3.1]nonane (0.5M in THF) was added dropwise at 0° C. and the reaction mixture was stirred for one hour at room temperature. 12 ml (12 mmol) of a sodium hydroxide solution (1 M) and 10 ml of a 30% hydrogen peroxide solution were then added successively and at 0° C. and the reaction mixture was stirred at room temperature for one hour. The reaction mixture was poured into water and extracted with ethyl ether and the organic phase was separated by settling, dried over magnesium sulfate and evaporated.

Workup

  1. stirringthe reaction mixture was stirred at room temperature for one hour
  2. extractionextracted with ethyl ether
  3. customthe organic phase was separated
  4. dry with materialdried over magnesium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-d8987d6504bf4a82a000144bd1943ee0
Source dataset
uspto-grants-1999_09
Patent number
US05952382

Reaction notes

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