Ethyl Acetate → HCID 87378695, compound

HRID 1805743Notes

Reaction equation

HRID 1805743 reaction equation
I[C:2]1[C:15]2[CH:14]=[CH:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6]=2[CH:5]=[CH:4][CH:3]=1.[Si:16]([O:23][CH2:24][C:25]1[CH:26]=[C:27](B(O)O)[CH:28]=[C:29]([CH2:31][O:32][Si:33]([C:36]([CH3:39])([CH3:38])[CH3:37])([CH3:35])[CH3:34])[CH:30]=1)([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17].[OH-].[Na+].CCOC(C)=O>C1COCC1.O.C1C=CC(P([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C1C=CC(P([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.[Fe]>[Si:16]([O:23][CH2:24][C:25]1[CH:26]=[C:27]([C:9]2[CH:8]=[C:7]3[C:12](=[CH:11][CH:10]=2)[CH:13]=[CH:14][C:15]2[CH:2]=[CH:3][CH:4]=[CH:5][C:6]3=2)[CH:28]=[C:29]([CH2:31][O:32][Si:33]([C:36]([CH3:39])([CH3:38])[CH3:37])([CH3:35])[CH3:34])[CH:30]=1)([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 21709689HCID 21709689, compound2×HCID 44204091HCID 44204091, compound

Product 1

HCID 87378695HCID 87378695, compoundYield 107.2%

Reagents, catalysts & solvents 2

HCID 178477754HCID 178477754, compoundCatalystHCID 21881883Oxolane--water (1/1)Solvent2×

Procedure

0.122 g (5 mol %) of Pdcl2 (dppf) was added to 0.742 g (2.44 mmol) of iodophenanthrene in a darkroom, and dissolved with 12 ml of THF/H2O. 0.90 g (2.19 mmol) of 3,5-bis-tert-butyldimethylsilyloxymethyl Phenylboronic acid dissolved in 12 ml of THF/H2O was added, 3.66 ml (3 eq) of 2N NaOH aq was injected, the reaction was initiated in a 65° C. oil bath with light shielding, and the mixture was agitated for 24 hours. Completion of the reaction could not be confirmed because the raw material iodophenanthrene overlaps the target product in TLC (Hex:EtOAc=1:1). Fluorescence was confirmed with the naked eye. This was extracted with EtOAc, and the organic layer was washed with H2O, sat. NaHCO3 aq and sat. NaCl aq, and dried by addition of anhydrous NaSO4. The solvent was distilled off under reduced pressure to obtain 1.2749 g of a mixture of the target product and iodophenanthrene.

Workup

  1. additionwas added
  2. customwas initiated in a 65° C.
  3. customCompletion of the reaction could not
  4. extractionThis was extracted with EtOAc
  5. washthe organic layer was washed with H2O, sat. NaHCO3 aq and sat. NaCl aq
  6. dry with materialdried by addition of anhydrous NaSO4
  7. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-a46711861b0047da8b6587a106c33662
Source dataset
uspto-grants-2013_01
Patent number
US08354515B2

Reaction notes

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