Methoxymethyl-triphenylphosphonium chloride → 2-(2-Methoxy-1-methyl-vinyl)-3-methyl-5-(4-trifluoromethyl-phenyl)-thiophene

HRID 1785236Notes

Reaction equation

HRID 1785236 reaction equation
[Cl-].[CH3:2][O:3][CH2:4][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CC(C)([O-])C.[K+].[CH3:30][C:31]1[CH:35]=[C:34]([C:36]2[CH:41]=[CH:40][C:39]([C:42]([F:45])([F:44])[F:43])=[CH:38][CH:37]=2)[S:33][C:32]=1[C:46](=O)[CH3:47]>C1(C)C=CC=CC=1.C1COCC1>[CH3:2][O:3][CH:4]=[C:46]([C:32]1[S:33][C:34]([C:36]2[CH:41]=[CH:40][C:39]([C:42]([F:45])([F:44])[F:43])=[CH:38][CH:37]=2)=[CH:35][C:31]=1[CH3:30])[CH3:47]

Participants

5

Reactant 3

HCID 2723798Methoxymethyl-triphenylphosphonium chlorideHCID 23665647Potassium tert-butoxideHCID 575950001-[3-Methyl-5-(4-trifluoromethyl-phenyl)-thiophen-2-yl]-ethanone

Product 1

HCID 688523672-(2-Methoxy-1-methyl-vinyl)-3-methyl-5-(4-trifluoromethyl-phenyl)-thiophene

Reagents, catalysts & solvents 1

HCID 22635083Tetrahydrofuran tolueneSolvent

Procedure

To a solution of (methoxymethyl)triphenyl phosphonium chloride (3.96 g, 10.76 mmole) in toluene/THF (2:1, 60 mL), is added potassium t-butoxide (1.21 g, 10.76 mmole) in one portion and stirred for 30 minutes. To the resulting ylide, is injected into a solution of 1-[3-Methyl-5-(4-trifluoromethyl-phenyl)-thiophen-2-yl]-ethanone (1.53 g, 5.38 mmole). The reaction is stirred for 2 hours, 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 2-(2-Methoxy-1-methyl-vinyl)-3-methyl-5-(4-trifluoromethyl-phenyl)-thiophene as brown oil. The generated vinyl ether is treated with concentrated HCl(aq) (2 mL) in THF(60 mL) at 60° C. for 2 hours. The solvents are removed on rota vapor, and the residue is purified on a silica gel column, eluting with 0-20% ethyl acetate in hexane and concentrated to provide the titled compound as colorless oil.

Workup

  1. stirringThe reaction is stirred for 2 hours
  2. concentrationconcentrated on rota vapor
  3. customThe residue is purified on a silica gel column
  4. washeluting with 0-10% ethyl acetate in hexane
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-62425f70050d42c1a414238fad5cd29a
Source dataset
uspto-grants-2009_03
Patent number
US07504433B2

Reaction notes

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