Phosphonium → HCID 54195630, compound

HRID 2228001Notes

Reaction equation

HRID 2228001 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9](=O)[CH2:10][N:11]2[CH:15]=[CH:14][N:13]=[CH:12]2)=[CH:4][CH:3]=1.[Br-].[CH3:18][O:19][C:20]([C:22]1[CH:23]=[C:24]([CH:45]=[CH:46][CH:47]=1)[CH2:25][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:21].CC(C)([O-])C.[K+].[PH4+]>ClCCl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH2:9][CH2:10][N:11]2[CH:15]=[CH:14][N:13]=[CH:12]2)=[CH:25][C:24]2[CH:23]=[C:22]([CH:47]=[CH:46][CH:45]=2)[C:20]([O:19][CH3:18])=[O:21])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 5460504PhosphoniumHCID 10051285Phosphonium, [[3-(methoxycarbonyl)phenyl]methyl]triphenyl-, bromideHCID 23665647Potassium tert-butoxide2×HCID 43797885HCID 43797885, compound

Product 1

HCID 54195630HCID 54195630, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of product from step C (2.00 g, 9.17 mmol) in dichloromethane (25 ml) was added 3-methoxycarbonylbenzyltriphenylphosphonium bromide (4.50 g, 9.17 mmol) and potassium tert-butoxide (1.03 g, 9.17 mmol). The mixture was stirred at room temperature for 18 hrs. A further portion of the phosphonium salt (0.88 g, 1.83 mmol) and potassium tert-butoxide (0.21 g, 1.83 mmol) was added. After 16 hrs at room temperature the mixture was partitioned between brine (50 ml) and dichloromethane (50 ml). The organic phase was washed with brine (2×50 ml) and dried (MgSO4). Evaporation of the solvent left an orange gum which was purified by column chromatography on SiO2 (Merck 9385) eluting EtOAc/ammonia (1%) to give methyl 3-[2-(4-fluorophenyl)-4-(imidazol-1-yl)-but-1-enyl]-benzoate as Z isomer 0.57 g (18%), E isomer 0.38 g (12%) and a mixture of isomers 0.65 g (20%) as a yellow gum.

Workup

  1. customAfter 16 hrs at room temperature the mixture was partitioned between brine (50 ml) and dichloromethane (50 ml)
  2. washThe organic phase was washed with brine (2×50 ml)
  3. dry with materialdried (MgSO4)
  4. customEvaporation of the solvent
  5. waitleft an orange gum which
  6. customwas purified by column chromatography on SiO2 (Merck 9385)
  7. washeluting EtOAc/ammonia (1%)

Sources & evidence

ORD record
ord-18472fa1adba45f3940f27ac44599eab
Source dataset
uspto-grants-2002_07
Patent number
US06414145B1

Reaction notes

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