HCID 19432964, compound → HCID 19432959, compound

HRID 1736418Notes

Reaction equation

HRID 1736418 reaction equation
[CH2:1]([Li])CCC.[F:6][C:7]1[CH:12]=[C:11]([F:13])[CH:10]=[CH:9][C:8]=1[C:14]1([C:17]([C:19]2[CH:20]=[CH:21][C:22]([S:25][CH3:26])=[N:23][CH:24]=2)=O)[CH2:16][O:15]1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[F:6][C:7]1[CH:12]=[C:11]([F:13])[CH:10]=[CH:9][C:8]=1[C:14]1([C:17]([C:19]2[CH:20]=[CH:21][C:22]([S:25][CH3:26])=[N:23][CH:24]=2)=[CH2:1])[CH2:16][O:15]1

Participants

5

Reactant 2

HCID 19432964HCID 19432964, compoundHCID 178418339Butyllithium

Product 1

HCID 19432959HCID 19432959, compoundYield 90.7%

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A suspension of methyltriphenylphosphonium bromide (5.0 g, 14 mmol) in THF (70 ml) was treated with n-butyllithium (2.5M solution in hexane, 5.6 ml, 14 mmol) under an atmosphere of nitrogen at -70° C. After 15 minutes at -70° C. the mixture was warmed to 0° C. and then was treated dropwise with a solution of the product of part (v) (3.9 g, 13 mmol) in THF (40 ml). The mixture was stirred at room temperature for 18 hours and then evaporated under reduced pressure. The residue was partitioned between dichloromethane (50 ml) and water (30 ml). The organic phase was dried (MgSO4) and evaporated under reduced pressure. The crude product was purified by flash chromatography on silica by elution with ether/hexane (1:4) to provide the title compound as an orange oil, (3.6 g).

Workup

  1. customevaporated under reduced pressure
  2. customThe residue was partitioned between dichloromethane (50 ml) and water (30 ml)
  3. dry with materialThe organic phase was dried (MgSO4)
  4. customevaporated under reduced pressure
  5. customThe crude product was purified by flash chromatography on silica by elution with ether/hexane (1:4)

Sources & evidence

ORD record
ord-cd69c6fe409a4b61aa41100ba556f913
Source dataset
uspto-grants-1996_07
Patent number
US05541203

Reaction notes

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