2-Phenyl-1,3-thiazole-5-carbaldehyde → (2-Phenylthiazol-5-yl)(3,4,5-trimethoxyphenyl)methanol

HRID 70017Notes

Reaction equation

HRID 70017 reaction equation
[C:1]1([C:7]2[S:8][C:9]([CH:12]=[O:13])=[CH:10][N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:14][O:15][C:16]1[CH:17]=[C:18]([Mg]Br)[CH:19]=[C:20]([O:24][CH3:25])[C:21]=1[O:22][CH3:23]>C1COCC1>[C:1]1([C:7]2[S:8][C:9]([CH:12]([C:18]3[CH:19]=[C:20]([O:24][CH3:25])[C:21]([O:22][CH3:23])=[C:16]([O:15][CH3:14])[CH:17]=3)[OH:13])=[CH:10][N:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 27637062-Phenyl-1,3-thiazole-5-carbaldehydeHCID 178492974HCID 178492974, compound

Product 1

HCID 53364129(2-Phenylthiazol-5-yl)(3,4,5-trimethoxyphenyl)methanolYield 72.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2-phenylthiazole-5-carbaldehyde 38e (0.567 g, 3 mmoL) in 15 mL THF was added a THF solution of 3,4,5-trimethoxyphenylmagnesiumbromide (0.5 N, 6.5 mL, 3.25 mmol) at 0° C. The mixture was allowed to stir for 30 min and quenched with satd. NH4Cl, extracted with ethyl ether, dried with MgSO4. The solvent was removed under reduced pressure to yield a crude product, which was purified by column chromatography to obtain pure compound 40e (72.9%). 1H NMR (CDCl3) δ 7.90 (m, 2H), 7.64 (s, 1H), 7.41 (m, 3H), 6.69 (s, br, 2H), 6.04 (s, 1H), 3.86 (s, 6H), 3.85 (s, 3H), 1.57 (d, 1H, J=5.5 Hz); MS (ESI) m/z 358.1 (M+Na)+.

Workup

  1. customquenched with satd
  2. extractionNH4Cl, extracted with ethyl ether
  3. dry with materialdried with MgSO4
  4. customThe solvent was removed under reduced pressure
  5. customto yield a crude product, which
  6. customwas purified by column chromatography

Sources & evidence

ORD record
ord-bdfd3bf29ba44d8eaa83d5ed11526e6e
Source dataset
uspto-grants-2014_09
Patent number
US08822513B2

Reaction notes

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