Ethyl Acetate → HCID 131730736, compound

HRID 455995Notes

Reaction equation

HRID 455995 reaction equation
[C:1]([SiH2:5][O:6][C:7]([CH3:34])([CH3:33])[C:8]12[O:15][C:12]([C:16]([CH3:24])([CH3:23])[O:17][SiH2:18][C:19]([CH3:22])([CH3:21])[CH3:20])([CH:13]=[CH:14]1)[CH2:11][C:10](OS(C(F)(F)F)(=O)=O)=[CH:9]2)([CH3:4])([CH3:3])[CH3:2].CC1(C)C(C)(C)OB([C:43]2[CH:48]=[CH:47][C:46]([NH2:49])=[CH:45][CH:44]=2)O1.C([O-])([O-])=O.[Na+].[Na+].CCOC(C)=O>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:1]([SiH2:5][O:6][C:7]([CH3:34])([CH3:33])[C:8]12[O:15][C:12]([C:16]([CH3:23])([CH3:24])[O:17][SiH2:18][C:19]([CH3:21])([CH3:22])[CH3:20])([CH:13]=[CH:14]1)[CH2:11][C:10]([C:43]1[CH:48]=[CH:47][C:46]([NH2:49])=[CH:45][CH:44]=1)=[CH:9]2)([CH3:3])([CH3:2])[CH3:4]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 27346204-(Tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 131730734HCID 131730734, compound

Product 1

HCID 131730736HCID 131730736, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of trifluoromethanesulfonic acid 1,5-bis-(tert-butyl-dimethyl-silanyloxymethyl)-8-oxa-bicyclo[3.2.1]octa-2,6-dien-3-yl ester (as prepared in the previous step, 1.22 g, 2.24 mmol), Pd(PPh3)4 (259 mg, 0.224 mmol) and 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenylamine (540 mg, 2.46 mmol) in 20 mL of 1,4-dioxane was added 2.0 M aqueous Na2CO3 solution (9.0 mL, 18 mmol). The resulting mixture was stirred at 80° C. for 2 h and then cooled to RT. Treated with 100 mL of EtOAc, the mixture was washed with H2O (3×20 mL), brine (20 mL) and dried (Na2SO4). Removal of the solvent under reduced pressure followed by flash chromatography of the residue on silica gel (1:1 hexane/DCM-DCM) gave 802 mg (73% for two steps) of the title compound as a light brown oil. Mass spectrum (ESI, m/z): Calcd. for C27H45NO3Si2, 488.3 (M+H), found 488.4.

Workup

  1. temperaturecooled to RT
  2. washthe mixture was washed with H2O (3×20 mL), brine (20 mL)
  3. dry with materialdried (Na2SO4)
  4. customRemoval of the solvent under reduced pressure

Sources & evidence

ORD record
ord-35ee9a6acbb34d098f3f80482d2a3fc6
Source dataset
uspto-grants-2013_07
Patent number
US08497376B2

Reaction notes

Loading…