Tetrafluoroboric acid → HCID 178426799, compound

HRID 1162169Notes

Reaction equation

HRID 1162169 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH:10]2[C:15](=[O:16])[CH2:14][C:13]([CH3:18])([CH3:17])[CH2:12][C:11]2=[O:19])=[CH:2]1.[F:20][B-:21]([F:24])([F:23])[F:22].[H+].[CH2:26](OC(OCC)OCC)C>C(OCC)C>[F:20][B-:21]([F:24])([F:23])[F:22].[CH3:18][C:13]1([CH3:17])[CH2:14][C:15]2[O+:16]=[CH:26][C:2]3[NH:1][C:9]4[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=4[C:3]=3[C:10]=2[C:11](=[O:19])[CH2:12]1

Participants

5

Reactant 3

HCID 28118Tetrafluoroboric acidHCID 31214Ethyl orthoformateHCID 7944562-(1H-indol-3-yl)-5,5-dimethylcyclohexane-1,3-dione

Product 1

HCID 178426799HCID 178426799, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a suspension of 2-(1H-indol-3-yl)-5,5-dimethylcyclohexane-1,3-dione of Example 1f (2.5 g, 9.8 mmol) in diethoxymethoxyethane (20 mL), tetrafluoroboric acid (54 wt % solution in diethyl ether, 2 mL, 14.5 mmol) was added in two portions under stirring. The mixture was stirred at room temperature for 2 h and diluted with diethyl ether (20 mL). The solid product was filtered off, washed with diethyl ether and air-dried at room temperature to give 2.4 g (70%) of the product as red crystals, which was used in the next step without purification.

Workup

  1. additionwas added in two portions
  2. stirringThe mixture was stirred at room temperature for 2 h
  3. filtrationThe solid product was filtered off
  4. washwashed with diethyl ether
  5. customair-dried at room temperature

Sources & evidence

ORD record
ord-f0074aa5f9024d7e94e5b38964e757e0
Source dataset
uspto-grants-2010_10
Patent number
US07820691B2

Reaction notes

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