Tetrahydrofuran → [(1,4-Dioxa-spiro[4.5]dec-8-yl)-thiophen-2-yl-methyl]-dimethylamine

HRID 557517Notes

Reaction equation

HRID 557517 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.[S:22]1C=[CH:25][CH:24]=[C:23]1[Mg]Br.[Cl-].[NH4+]>C(OCC)C.O>[O:14]1[C:10]2([CH2:15][CH2:16][CH:7]([CH:4]([N:2]([CH3:3])[CH3:1])[C:5]3[S:22][CH:23]=[CH:24][CH:25]=3)[CH2:8][CH2:9]2)[O:11][CH2:12][CH2:13]1

Participants

7

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 25517Ammonium ChlorideHCID 57839521Dimethylamino-(1,4-dioxaspiro[4.5]dec-8-yl)-acetonitrileHCID 178418438HCID 178418438, compound

Product 1

HCID 66703411[(1,4-Dioxa-spiro[4.5]dec-8-yl)-thiophen-2-yl-methyl]-dimethylamine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of the aminonitrile 3 (2.24 g, 10 mmol) in abs. THF (10 ml) was added dropwise, under argon and while cooling with ice, to a 1M solution of thiophen-2-yl-magnesium bromide in THF (20 ml, 20 mmol), and stirring was carried out for 20 h at RT. For working up the reaction mixture, saturated ammonium chloride solution (10 ml) and water (10 ml) were added, while cooling with ice, and extraction with diethyl ether (3×10 ml) was carried out. The organic phase was washed with water and saturated sodium chloride solution, dried and concentrated.

Workup

  1. additionwere added
  2. washThe organic phase was washed with water and saturated sodium chloride solution
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-721709ed933f420fafbed42afc5bec29
Source dataset
uspto-grants-2011_11
Patent number
US08058475B2

Reaction notes

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