Chlorotriethylsilane → HCID 87824967, compound

HRID 853120Notes

Reaction equation

HRID 853120 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([OH:17])([C:13]([F:16])([F:15])[F:14])[C:9]([F:12])([F:11])[F:10])=[CH:4][CH:3]=1.C1CCN2C(=NCCC2)CC1.[Si:29](Cl)([CH2:34][CH3:35])([CH2:32][CH3:33])[CH2:30][CH3:31]>CN(C=O)C>[F:16][C:13]([F:14])([F:15])[C:8]([C:5]1[CH:4]=[CH:3][C:2]([NH2:1])=[CH:7][CH:6]=1)([O:17][Si:29]([CH2:34][CH3:35])([CH2:32][CH3:33])[CH2:30][CH3:31])[C:9]([F:10])([F:11])[F:12]

Participants

5

Reactant 3

HCID 13819ChlorotriethylsilaneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 5778012-(4-Aminophenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol

Product 1

HCID 87824967HCID 87824967, compoundYield 90.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 10 g (38.6 mmol) of 2-(4-amino-phenyl)-1,1,1,3,3,3-hexafluoro-propan-2-ol in 100 mL of DMF was treated with 6.3 mL (42.4 mmol) of DBU and then dropwise with 6.5 mL (38.6 mmol) of TESCl. After stirring the mixture at RT overnight the solvent was partially evaporated i.v. Distribution of the crude mixture between a diluted aqueous solution of NaOH and Et2O and drying of the combined organic phases over Na2SO4 gave 13 g (90%) of 4-(2,2,2-trifluoro-1-triethylsilanyloxy-1-trifluoromethyl-ethyl)-phenylamine as a colorless oil, MS: 374 (M+H)+.

Workup

  1. dry with materialDistribution of the crude mixture between a diluted aqueous solution of NaOH and Et2O and drying of the combined organic phases over Na2SO4

Sources & evidence

ORD record
ord-6dd1e1b96f064a0fbe37601021933f9d
Source dataset
uspto-grants-2007_08
Patent number
US07253282B2

Reaction notes

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