Styrene Oxide → HCID 86602504, compound

HRID 854480Notes

Reaction equation

[CH2:1]([NH:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]([O:19][Si:20]([CH2:25][CH3:26])([CH2:23][CH3:24])[CH2:21][CH3:22])([C:15]([F:18])([F:17])[F:16])[C:11]([F:14])([F:13])[F:12])=[CH:6][CH:5]=1)[CH3:2].[C:27]1([CH:33]2[CH2:35][O:34]2)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.Cl([O-])(=O)(=O)=O.[Li+].[NH4+].[Cl-]>C(#N)C.CCOCC>[CH2:1]([N:3]([C:4]1[CH:5]=[CH:6][C:7]([C:10]([O:19][Si:20]([CH2:21][CH3:22])([CH2:25][CH3:26])[CH2:23][CH3:24])([C:15]([F:16])([F:17])[F:18])[C:11]([F:12])([F:13])[F:14])=[CH:8][CH:9]=1)[CH:33]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH2:35][OH:34])[CH3:2]

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of 4 g (10 mmol) of ethyl-[4-(2,2,2-trifluoro-1-triethylsilanyloxy-1-trifluoromethyl-ethyl)-phenyl]-amine (example 1.1) in 12 mL of acetonitrile was treated with 2.3 mL (20 mmol) of racemic phenyloxirane and 2.12 g (20 mmol) of lithiumperchlorate. The mixture was stirred overnight at 80° C. in a sealed tube. The crude was distributed between saturated aqueous NH4Cl and Et2O and the combined organic phases were dried over Na2SO4 and evaporated. Column chromatography on silica gel with n-heptane/EtOAc 9:1 yielded 3.5 g (66%) of 2-{ethyl-[4-(2,2,2-trifluoro-1-triethylsilanyloxy-1-trifluoromethyl-ethyl)-phenyl]-amino}-2-phenyl-ethanol, light yellow oil, MS: 522 (MH+) and 0.475 g (9%) of 2-{ethyl-[4-(2,2,2-trifluoro-1-triethylsilanyloxy-1-trifluoromethyl-ethyl)-phenyl]-amino}-1-phenyl-ethanol, light yellow oil, MS: 522 (MH+).

Workup

dry with materialthe combined organic phases were dried over Na2SO4
customevaporated

Sources & evidence

ORD record: ord-14c13d4020dc4f8fbea57d6433f4da11
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07259178B2

Reaction notes

Loading…