[3-(2,6-Dichloro-5-isopropyl-pyrimidin-4-yloxy)-5-methyl-phenyl]-methanol → 3-(2,6-Dichloro-5-isopropyl-pyrimidin-4-yloxy)-5-methyl-benzaldehyde

HRID 426200Notes

Reaction equation

HRID 426200 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([O:8][C:9]2[CH:10]=[C:11]([CH2:16][OH:17])[CH:12]=[C:13]([CH3:15])[CH:14]=2)[C:5]([CH:18]([CH3:20])[CH3:19])=[C:4]([Cl:21])[N:3]=1.C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O>>[Cl:1][C:2]1[N:7]=[C:6]([O:8][C:9]2[CH:10]=[C:11]([CH:12]=[C:13]([CH3:15])[CH:14]=2)[CH:16]=[O:17])[C:5]([CH:18]([CH3:19])[CH3:20])=[C:4]([Cl:21])[N:3]=1

Participants

3

Reactant 2

HCID 59184707[3-(2,6-Dichloro-5-isopropyl-pyrimidin-4-yloxy)-5-methyl-phenyl]-methanolHCID 178418287HCID 178418287, compound

Product 1

HCID 591846443-(2,6-Dichloro-5-isopropyl-pyrimidin-4-yloxy)-5-methyl-benzaldehydeYield 73%

Procedure

A mixture of [3-(2,6-dichloro-5-isopropyl-pyrimidin-4-yloxy)-5-methyl-phenyl]-methanol (2.36 g, 7.22 mmol), PCC (1.56 g, 7.22 mmol), and dried celite (2 g) was stirred in dichloromethane (20 ml) for 2 hr. at room temperature. The mixture was then filtered through a short silica gel pad and washed with EA. The combined filtrate was evaporated in vacuo and the residue was purified by silica gel column chromatography (eluent, EA:hexanes (1:15)) to afford 1.71 g (73%) of a pale yellow syrup. 1H NMR (200 MHz, CDCl3) δ 1.42 (6H, d, J=7.2 Hz), 2.49 (3H, s), 3.61 (1H, m), 7.20 (1H, s), 7.44 (1H, s), 7.62 (1H, s), 10.01 (1H, s).

Workup

  1. customdried celite (2 g)
  2. customat room temperature
  3. filtrationThe mixture was then filtered through a short silica gel pad
  4. washwashed with EA
  5. customThe combined filtrate was evaporated in vacuo
  6. customthe residue was purified by silica gel column chromatography (eluent, EA:hexanes (1:15))

Sources & evidence

ORD record
ord-68cb5c1490394105b06311ddabffa3b6
Source dataset
uspto-grants-2012_01
Patent number
US08106064B2

Reaction notes

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