Ethyl orthoformate → HCID 68600565, compound

HRID 2090213Notes

Reaction equation

HRID 2090213 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:17]3[C:16](=[O:18])[NH:15][CH:14]=[CH:13][C:12]=3[NH:11][C:10]([CH3:19])=[C:9]2[C:20]([O:22][CH2:23][CH2:24][C:25]#[N:26])=[O:21])=[C:4]([O:27][C:28]([F:31])([F:30])[F:29])[CH:3]=1.C(OCC)(OCC)O[CH2:34][CH3:35]>S(=O)(=O)(O)O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:17]3[C:12](=[CH:13][CH:14]=[N:15][C:16]=3[O:18][CH2:34][CH3:35])[NH:11][C:10]([CH3:19])=[C:9]2[C:20]([O:22][CH2:23][CH2:24][C:25]#[N:26])=[O:21])=[C:4]([O:27][C:28]([F:30])([F:29])[F:31])[CH:3]=1

Participants

4

Reactant 2

HCID 31214Ethyl orthoformateHCID 68599964HCID 68599964, compound

Product 1

HCID 68600565HCID 68600565, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Conditions

Temperature
130 °C

Procedure

7.30 g (13.19 mmol) of the compound from Example 34A are suspended in 150 ml of triethyl orthoformate and heated to 130° C. Then, over a total period of 7 hours, 15 drops of concentrated sulfuric acid are added each hour to the reaction mixture. It is then stirred at the same temperature overnight. After cooling, excess orthoester is removed in a rotary evaporator, and the crude product is purified by column chromatography (silica gel; mobile phase: cyclohexane/ethyl acetate 1:1). 4.59 g (64% of theory) of the title compound are obtained.

Workup

  1. temperatureAfter cooling
  2. customexcess orthoester is removed in a rotary evaporator
  3. customthe crude product is purified by column chromatography (silica gel; mobile phase: cyclohexane/ethyl acetate 1:1)

Sources & evidence

ORD record
ord-abef9f7c40c54bd3bb8c2f1db8e28526
Source dataset
uspto-grants-2013_05
Patent number
US08436180B2

Reaction notes

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