Water → HCID 57708991, compound

HRID 546813Notes

Reaction equation

HRID 546813 reaction equation
[Cl-].[Li+].[C:3]([Si:7]([CH3:44])([CH3:43])[O:8][CH:9]([C:39]([CH3:42])([CH3:41])[CH3:40])[CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]([C:23]2[CH:28]=[CH:27][C:26](OS(C(F)(F)F)(=O)=O)=[C:25]([CH3:37])[CH:24]=2)([CH2:21][CH3:22])[CH2:19][CH3:20])=[CH:14][C:13]=1[CH3:38])([CH3:6])([CH3:5])[CH3:4].O.[C:46](OCC)(=O)[CH3:47].[CH2:52]([CH2:55][O:56][CH3:57])[O:53]C>C1(C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)[Pd][P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:3]([Si:7]([CH3:44])([CH3:43])[O:8][CH:9]([C:39]([CH3:41])([CH3:42])[CH3:40])[CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]([C:23]2[CH:28]=[CH:27][C:26]([C:57]3[O:56][C:55]([CH:52]=[O:53])=[CH:47][CH:46]=3)=[C:25]([CH3:37])[CH:24]=2)([CH2:19][CH3:20])[CH2:21][CH3:22])=[CH:14][C:13]=1[CH3:38])([CH3:6])([CH3:5])[CH3:4]

Participants

7

Reactant 5

HCID 962WaterHCID 80711,2-DimethoxyethaneHCID 8857Ethyl AcetateHCID 433294Lithium ChlorideHCID 57708953HCID 57708953, compound

Product 1

HCID 57708991HCID 57708991, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 178419050HCID 178419050, compoundCatalyst

Conditions

Temperature
60 °C

Procedure

Lithium chloride (593 mg, 14 mmol), bis(triphenylphosphine)palladium (II) dichloride (123 mg, 0.175 mmol) and 5-tributylstannyl-1-furan-2-carbaldehyde (2.02 mg, 5.25 mmol) were added to a suspension 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 3-(5); 1.10 g, 1.75 mmol) in dimethoxyethane (5.3 mL), and the mixture was stirred at 60° C. for 15 hours. Water and ethyl acetate were added to the mixture. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography (hexane only to hexane/ethyl acetate=90/1) to give the title compound (2404 mg, 24%).

Workup

  1. washThe organic layer was washed with brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel chromatography (hexane only to hexane/ethyl acetate=90/1)

Sources & evidence

ORD record
ord-f753b16bec4f4ad7963d2aa8c9a76dca
Source dataset
uspto-grants-2011_05
Patent number
US07935688B2

Reaction notes

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