Hydrochloric Acid → t-Butyl-(4-fluoro-3-methoxybenzyloxy)diphenylsilane

HRID 2079216Notes

Reaction equation

HRID 2079216 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][OH:9])=[CH:4][C:3]=1[O:10][CH3:11].N1C=CN=C1.C(O)(=O)C.C(OC1C=C(C(NC2C=CC(C(N)=N)=CC=2)C2NC(=O)N(C3N=CC=CN=3)N=2)C=CC=1OC)C.[C:55]([Si:59](Cl)([C:66]1[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=1)[C:60]1[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=1)([CH3:58])([CH3:57])[CH3:56].Cl>C(OCC)(=O)C>[C:55]([Si:59]([O:9][CH2:8][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[C:3]([O:10][CH3:11])[CH:4]=1)([C:66]1[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=1)[C:60]1[CH:61]=[CH:62][CH:63]=[CH:64][CH:65]=1)([CH3:58])([CH3:56])[CH3:57]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 795ImidazoleHCID 94078tert-ButyldiphenylchlorosilaneHCID 593590(4-Fluoro-3-methoxyphenyl)methanolHCID 1363662594-{[(3-ethoxy-4-methoxyphenyl)-(5-oxo-1-pyrimidin-2-yl-4,5-dihydro-1H-[1,2,4]triazol-3-yl)methyl]amino}benzamidine acetate

Product 1

HCID 67097579t-Butyl-(4-fluoro-3-methoxybenzyloxy)diphenylsilane

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

After dissolving 9.17 g of (4-fluoro-3-methoxyphenyl)methanol [CAS No. 128495-45-4] in 100 ml of DMT, 5g of imidazole and 17g of t-butyl -chlorodiphenylsilane were added and the mixture was stirred overnight at room temperature. Next, 1N hydrochloric acid was added to the reaction mixture, and extraction was performed with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate. The desiccating agent was filtered off and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate-heptane) to give t-butyl-(4-fluoro-3-methoxybenzyloxy)diphenylsilane as an oil.

Workup

  1. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  2. filtrationThe desiccating agent was filtered off
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (ethyl acetate-heptane)

Sources & evidence

ORD record
ord-3571530c93cb4b3ca4c1cc3c21131d56
Source dataset
uspto-grants-2011_04
Patent number
US07928228B2

Reaction notes

Loading…