Water → HCID 23445654, compound

HRID 1280886Notes

Reaction equation

HRID 1280886 reaction equation
ICO[C:4]1[CH:5]=[C:6]([CH:9]=[C:10]([CH3:12])[CH:11]=1)[CH:7]=[O:8].[C:13]1(B(O)O)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.O.O.O.O.O.O.O.O.[OH-].[Ba+2].[OH-].O.[CH3:34][O:35]CCOC>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:34][O:35][C:11]1[C:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:5][C:6]([CH:7]=[O:8])=[CH:9][C:10]=1[CH3:12]

Participants

7

Reactant 5

HCID 962WaterHCID 80711,2-DimethoxyethaneHCID 66827Phenylboronic AcidHCID 17749109Barium hydroxide, octahydrateHCID 18426310HCID 18426310, compound

Product 1

HCID 23445654HCID 23445654, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Procedure

The title compound was prepared according to the procedure in Example 2, step 3 using 3-iodomethoxy-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:H2O. 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) δ 2.37 (s, 3H), 3.39 (s, 3H), 7.42-7.59 (m, 5H), 7.74-7.79 (m, 2H), 9.96 (s, 1H).

Workup

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

Sources & evidence

ORD record
ord-95125c7269314c02abfa282feea19e7e
Source dataset
uspto-grants-2002_09
Patent number
US06451845B1

Reaction notes

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