Ethylene Glycol → HCID 21951267, compound

HRID 2215616Notes

Reaction equation

HRID 2215616 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]([CH3:14])=[C:6]2[C:10]=1[C:9](=[O:11])[CH:8]([CH2:12][CH3:13])[CH2:7]2.[C:15]([C:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=1)([CH3:18])([CH3:17])[CH3:16].C(=O)([O-])[O-].[Na+].[Na+].C(O)CO>O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1C=C(S([O-])(=O)=O)C=C(P(C2C=CC=C(S([O-])(=O)=O)C=2)C2C=CC=C(S([O-])(=O)=O)C=2)C=1.[Na+].[Na+].[Na+]>[CH2:12]([CH:8]1[CH2:7][C:6]2[C:10](=[C:2]([C:22]3[CH:23]=[CH:24][C:19]([C:15]([CH3:18])([CH3:17])[CH3:16])=[CH:20][CH:21]=3)[CH:3]=[CH:4][C:5]=2[CH3:14])[C:9]1=[O:11])[CH3:13]

Participants

8

Reactant 4

HCID 174Ethylene GlycolHCID 10340Sodium CarbonateHCID 27343204-tert-Butylphenylboronic acidHCID 21951281HCID 21951281, compound

Product 1

HCID 21951267HCID 21951267, compoundYield 105.7%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 6099338Trisodium 3,3',3''-phosphinetriyltris(benzene-1-sulphonate)CatalystHCID 962WaterSolvent2×

Procedure

Using a method analogous to Example 1d, 29.0 g (138.96 mmol) of 7-chloro-2-ethyl-4-methyl-1-indanone (1b), 29.7 g (166.8 mmol) of 4-tert-butylphenylboronic acid, 36.8 g (347.3 mmol) of sodium carbonate, 300 ml of ethylene glycol and 40 ml of water were reacted at 80° C. in the presence of a freshly prepared catalyst solution of 156 mg (0.695 mmol) of palladium acetate, 3.5 ml (2.08 mmol) of an aqueous TPPTS solution (0.6 molar) in 19 ml of water. 45.00 g of (2c) were isolated.

Sources & evidence

ORD record
ord-1e49b019b4b64a6a99ea6ff5bd4573d7
Source dataset
uspto-grants-2006_09
Patent number
US07109278B2

Reaction notes

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