Tetrabutylammonium Fluoride → HCID 86704549, compound

HRID 633462Notes

Reaction equation

HRID 633462 reaction equation
[Si]([O:8][CH2:9][C:10]1([CH2:28][O:29][Si](C(C)(C)C)(C)C)[O:15][C:14]2[CH:16]=[CH:17][C:18]([N+:20]([O-:22])=[O:21])=[CH:19][C:13]=2[N:12]2[C:23](=[O:27])[N:24]([CH3:26])[N:25]=[C:11]12)(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[OH:8][CH2:9][C:10]1([CH2:28][OH:29])[O:15][C:14]2[CH:16]=[CH:17][C:18]([N+:20]([O-:22])=[O:21])=[CH:19][C:13]=2[N:12]2[C:23](=[O:27])[N:24]([CH3:26])[N:25]=[C:11]12

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86704548HCID 86704548, compound

Product 1

HCID 86704549HCID 86704549, compoundYield 92.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

4,4-Bis(((tert-butyldimethylsilyl)oxy)methyl)-2-methyl-8-nitro-2,4-dihydro-1H-benzo[b][1,2,4]triazolo[4,3-d][1,4]oxazin-1-one (3 g) was dissolved in THF (15 mL). 1.0 M TBAF in THF solution was added (14 mL, 2.5 eq.). The reaction solution was stirred at room temperature for one hour and then evaporated. The residue was purified by Combiflash chromatography (methanol in dichloromethane=0-20%) to give 4,4-bis(hydroxymethyl)-2-methyl-8-nitro-2,4-dihydro-1H-benzo[b][1,2,4]triazolo[4,3-d][1,4]oxazin-1-one (1.6 g).

Workup

  1. customevaporated
  2. customThe residue was purified by Combiflash chromatography (methanol in dichloromethane=0-20%)

Sources & evidence

ORD record
ord-233ead14a1ac4d40b4d249cf0d6d103c
Source dataset
uspto-grants-2016_04
Patent number
US09321763B2

Reaction notes

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