1,2-Dimethoxyethane → HCID 23445654, compound

HRID 1841308Notes

Reaction equation

HRID 1841308 reaction equation
I[C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([CH3:12])[C:9]=1[O:10][CH3:11])[CH:5]=[O:6].[C:13]1(B(O)O)[CH:18]=[CH:17]C=[CH:15][CH:14]=1.O.O.O.O.O.O.O.O.[OH-].[Ba+2].[OH-].[CH3:33]OCCOC>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:11][O:10][C:9]1[C:8]([C:12]2[CH:17]=[CH:18][CH:13]=[CH:14][CH:15]=2)=[CH:7][C:4]([CH:5]=[O:6])=[CH:3][C:2]=1[CH3:33]

Participants

6

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 66827Phenylboronic AcidHCID 17749109Barium hydroxide, octahydrateHCID 23445614HCID 23445614, compound

Product 1

HCID 23445654HCID 23445654, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Procedure

The tide compound was prepared according to the procedure in Example 2, step 3 using 3-iodo4-methoxy-5-methylbenzaldehyde (2.24 g, 8.11 mmol), phenylboronic acid (1.09 g, 8.92 mmol), palladium(II) acetate (36.4 mg, 0.162 mmol) and barium hydroxide octahydrate (3.83 g, 12.2 mmol) in DME:H20. Purification on Biotage KP-Sil eluting with 15% acetone/hexane gave 1.54 g (84%) of the title compound as a yellow oil. 1H NMR (DMSO-d6) δ2.37 (s, 3 H), 3.39 (s, 3 H), 7.42-7.59 (m, 5 H), 7.74-7.79 (m, 2 H), 9.96 (s, 1 H).

Workup

  1. customThe tide compound was prepared
  2. customPurification on Biotage KP-Sil
  3. washeluting with 15% acetone/hexane

Sources & evidence

ORD record
ord-f38ccfe4d9ba406ba018c9c6730c0c71
Source dataset
uspto-grants-2004_01
Patent number
US06683107B2

Reaction notes

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