Methoxymethyl-triphenylphosphonium chloride → 5-(2-Methoxy-1-methyl-vinyl)4-methyl-2-(4-trifluoromethyl-phenyl)-thiazole

HRID 860614Notes

Reaction equation

HRID 860614 reaction equation
[Cl-].[CH3:2][O:3]C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[CH3:24][C:25]([CH3:28])([O-])[CH3:26].[K+].[CH3:30][C:31]1[N:32]=[C:33]([C:39]2[CH:44]=[CH:43][C:42]([C:45]([F:48])([F:47])[F:46])=[CH:41][CH:40]=2)[S:34]C=1C(=O)C>C1(C)C=CC=CC=1>[CH3:2][O:3][CH:24]=[C:25]([C:28]1[S:34][C:33]([C:39]2[CH:44]=[CH:43][C:42]([C:45]([F:48])([F:46])[F:47])=[CH:41][CH:40]=2)=[N:32][C:31]=1[CH3:30])[CH3:26]

Participants

5

Reactant 3

HCID 2723798Methoxymethyl-triphenylphosphonium chlorideHCID 98355181-{4-Methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl}ethan-1-oneHCID 23665647Potassium tert-butoxide

Product 1

HCID 690570175-(2-Methoxy-1-methyl-vinyl)4-methyl-2-(4-trifluoromethyl-phenyl)-thiazoleYield 74.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a solution of (methoxymethyl)triphenyl phosphonium chloride (15.5 g, 45.2 mmole) in toluene (330 mL) is added potassium t-butoxide (5.07 g, 45.2 mmole) in one portion and stirred for 30 minutes, then a solution of 1-[4-Methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-ethanone (8.6 g, 30.1 mmole) in toluene (20 mL) is added. The reaction is stirred for 4 hours, quenched by NH4Cl aqueous solution, extracted with ethyl acetate and then concentrated on rota vapor. The residue is purified on a silica gel column, eluting with 0–10% ethyl acetate in hexane and concentrated to provide the title compound (7.0 g).

Workup

  1. stirringThe reaction is stirred for 4 hours
  2. customquenched by NH4Cl aqueous solution
  3. extractionextracted with ethyl acetate
  4. concentrationconcentrated on rota vapor
  5. customThe residue is purified on a silica gel column
  6. washeluting with 0–10% ethyl acetate in hexane
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-45a86f831d23485caaba736e18f42279
Source dataset
uspto-grants-2006_12
Patent number
US07153878B2

Reaction notes

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