Sodium Carbonate → HCID 57709126, compound

HRID 546819Notes

Reaction equation

HRID 546819 reaction equation
[C:1]([Si:5]([CH3:42])([CH3:41])[O:6][CH:7]([C:37]([CH3:40])([CH3:39])[CH3:38])[CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([C:21]2[CH:26]=[CH:25][C:24](OS(C(F)(F)F)(=O)=O)=[C:23]([CH3:35])[CH:22]=2)([CH2:19][CH3:20])[CH2:17][CH3:18])=[CH:12][C:11]=1[CH3:36])([CH3:4])([CH3:3])[CH3:2].[CH3:43][O:44][C:45](=[O:63])[CH2:46][CH2:47][C:48]1[CH:53]=[CH:52][C:51](B2OC(C)(C)C(C)(C)O2)=[CH:50][CH:49]=1.C(=O)([O-])[O-].[Na+].[Na+].[Cl-].[NH4+]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].CN(C)C=O>[CH3:43][O:44][C:45](=[O:63])[CH2:46][CH2:47][C:48]1[CH:49]=[CH:50][C:51]([C:24]2[CH:25]=[CH:26][C:21]([C:16]([C:13]3[CH:14]=[CH:15][C:10]([CH2:9][CH2:8][CH:7]([O:6][Si:5]([C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:41])[CH3:42])[C:37]([CH3:40])([CH3:39])[CH3:38])=[C:11]([CH3:36])[CH:12]=3)([CH2:17][CH3:18])[CH2:19][CH3:20])=[CH:22][C:23]=2[CH3:35])=[CH:52][CH:53]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 25517Ammonium ChlorideHCID 11277714HCID 11277714, compoundHCID 57708953HCID 57708953, compound

Product 1

HCID 57709126HCID 57709126, compoundYield 10.1%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of trifluoromethanesulfonic acid 4-(1-{4-[3-(t-butyl-dimethyl-silanyloxy)-4,4-dimethyl-pentyl]-3-methyl-phenyl}-1-ethyl-propyl)-2-methyl-phenyl ester (Example 11-(1); 0.13 g, 0.2 mmol), 3-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propionic acid methyl ester (Example 11-(2); 0.06 g, 0.2 mmol), a [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II), dichloromethane complex (1:1) (0.01 g, 0.01 mmol), a sodium carbonate solution (2 M, 0.3 ml, 0.6 mmol) and N,N-dimethylformamide (1 mL) was stirred in a nitrogen atmosphere at 80° C. for four hours. A saturated aqueous ammonium chloride solution was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was then washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by preparative TLC (hexane/ethyl acetate=10/1) to give the title compound (0.013 g, 10%).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was then washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by preparative TLC (hexane/ethyl acetate=10/1)

Sources & evidence

ORD record
ord-d0f9f69bbdde405a8fe63493a02ae289
Source dataset
uspto-grants-2011_05
Patent number
US07935688B2

Reaction notes

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