Tetrahydrofuran → HCID 66703510, compound

HRID 1645392Notes

Reaction equation

HRID 1645392 reaction equation
[CH3:1][N:2]([CH:4]([CH:7]1[CH2:16][CH2:15][C:10]2([O:14][CH2:13][CH2:12][O:11]2)[CH2:9][CH2:8]1)[C:5]#N)[CH3:3].C1COCC1.[F:22][C:23]1[CH:24]=C([Mg]Br)[CH:26]=[CH:27][CH:28]=1.[Cl-].[NH4+]>O>[O:14]1[C:10]2([CH2:15][CH2:16][CH:7]([CH:4]([N:2]([CH3:3])[CH3:1])[C:5]3[CH:26]=[CH:27][CH:28]=[C:23]([F:22])[CH:24]=3)[CH2:8][CH2:9]2)[O:11][CH2:12][CH2:13]1

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 25517Ammonium ChlorideHCID 57839521Dimethylamino-(1,4-dioxaspiro[4.5]dec-8-yl)-acetonitrileHCID 178505773HCID 178505773, compound

Product 1

HCID 66703510HCID 66703510, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of the aminonitrile 4 (23.45 g, 104 mmol) in absol. THF (100 ml) was added dropwise to a 1 M solution of 3-fluorophenylmagnesium bromide in THF (208 ml, 208 mmol) under argon and while cooling with ice, and the mixture was stirred at RT for 20 hours. The reaction mixture was worked up by adding saturated ammonium chloride solution (100 ml) and water (100 ml) while cooling with ice, and extracting the mixture with diethyl ether (3×100 ml). The organic phase was washed with water and saturated sodium chloride solution, dried and concentrated.

Workup

  1. temperaturewhile cooling with ice
  2. temperaturewhile cooling with ice
  3. extractionextracting the mixture with diethyl ether (3×100 ml)
  4. washThe organic phase was washed with water and saturated sodium chloride solution
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e08e2296f57647e5bd4f7589fdb5098c
Source dataset
uspto-grants-2012_02
Patent number
US08124788B2

Reaction notes

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