Methanol → 4-Methyl-1-(4-methyl-thiazol-5-yl)-pentan-3-one

HRID 23445Notes

Reaction equation

HRID 23445 reaction equation
[CH3:1][CH:2]([CH3:13])[C:3](=[O:12])[CH:4]=[CH:5][C:6]1[S:10][CH:9]=[N:8][C:7]=1[CH3:11].CO>C1COCC1.[Pd].[O-]S([O-])(=O)=O.[Ba+2]>[CH3:1][CH:2]([CH3:13])[C:3](=[O:12])[CH2:4][CH2:5][C:6]1[S:10][CH:9]=[N:8][C:7]=1[CH3:11]

Participants

5

Reactant 2

HCID 887MethanolHCID 538148064-Methyl-1-(4-methyl-thiazol-5-yl)-pent-1-en-3-one

Product 1

HCID 225727814-Methyl-1-(4-methyl-thiazol-5-yl)-pentan-3-one

Reagents, catalysts & solvents 2

HCID 16218511Pd barium sulfateCatalystHCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared as described in General Method 3 using 1.73 g (8.86 mmol) of 4-methyl-1-(4-methyl-thiazol-5-yl)-pent-1-en-3-one (prepared in Example B-1) and 0.4 g of 5% Pd/BaSO4 in THF:MeOH (25 mL:25 mL). The crude product was chromatographed on silica gel, eluting with 2:1 hexane:EtOAc, to give the title compound. 1H NMR (CDCl3): δ 1.03 (d, 6H), 2.35 (s, 3H), 2.49-2.56 (m, 1H), 2.72 (t, 2H), 2.98 (t, 2H), 8.49 (s, 1H).

Workup

  1. customThe title compound was prepared
  2. customThe crude product was chromatographed on silica gel
  3. washeluting with 2:1 hexane

Sources & evidence

ORD record
ord-64c7a5fbcc5c441081fc34f25bb7de3b
Source dataset
uspto-grants-2005_02
Patent number
US06852711B2

Reaction notes

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