Water → HCID 89601563, compound

HRID 571973Notes

Reaction equation

HRID 571973 reaction equation
[CH3:1]C([O-])(C)C.[K+].[F:7][C:8]1[CH:17]=[CH:16][C:15]2[N:14]=[CH:13][C:12]([O:18][CH3:19])=[N:11][C:10]=2[C:9]=1[CH:20]=O.[NH4+].[Cl-].O>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[F:7][C:8]1[C:9]([CH:20]=[CH2:1])=[C:10]2[C:15]([N:14]=[CH:13][C:12]([O:18][CH3:19])=[N:11]2)=[CH:16][CH:17]=1

Participants

7

Reactant 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 23665647Potassium tert-butoxideHCID 73333326HCID 73333326, compound

Product 1

HCID 89601563HCID 89601563, compoundYield 90.3%

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Methyl triphenyl phosphonium bromide (154 g, 430 mmol) was suspended in THF (1 L) and cooled to 0° C. KOtBu (44.4 g, 400 mmol) was added in one portion and the yellow suspension was stirred at 0° C. for 15 min before a solution of 6-fluoro-3-methoxyquinoxaline-5-carbaldehyde (71 g, 340 mmol) in THF (550 mL) was added dropwise over 70 min. The mixture was stirred at 0° C. for 60 min. Sat. NH4Cl solution (250 mL) and water (250 mL) were added and the phases were separated. The org. layer was dried over MgSO4, filtered and concentrated to dryness. The residue was purified by two filtrations over a plug of silica gel (2×250 g) using an Hept/EA (2:1) mixture as eluent to afford the title alkene as an orange solid (62.7 g, 89% yield).

Workup

  1. additionwas added dropwise over 70 min
  2. customthe phases were separated
  3. dry with materiallayer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated to dryness
  6. filtrationThe residue was purified by two filtrations over a plug of silica gel (2×250 g)

Sources & evidence

ORD record
ord-14500385cb3f4dbb8a31a86dcc26e528
Source dataset
uspto-grants-2015_05
Patent number
US09029368B2

Reaction notes

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