Water → 4-(1-Azetidinyl)butanal dimethylacetal

HRID 865697Notes

Reaction equation

HRID 865697 reaction equation
[NH:1]1[CH2:4][CH2:3][CH2:2]1.[CH3:5][O:6][CH:7]([O:12][CH3:13])[CH2:8][CH2:9][CH2:10]Cl.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[CH3:5][O:6][CH:7]([O:12][CH3:13])[CH2:8][CH2:9][CH2:10][N:1]1[CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 10422AzetidineHCID 11430Potassium CarbonateHCID 1225364-Chloro-1,1-dimethoxybutane

Product 1

HCID 233745854-(1-Azetidinyl)butanal dimethylacetal

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of azetidine (2.0 g, 35.0 mmol), 4-chlorobutanal dimethylacetal (5.88 g, 39.0 mmol) and K2CO3 (5.38 g, 39.0 mmol), in anhydrous DMF (100ml), was stirred at room temperature for 72 h. Water (50 ml) was added and the mixture extracted with EtOAc (3×150 ml). The combined extracts were washed with H2O (3×50ml), dried (Na2SO4) and evaporated. The crude product was purified by distillation (1.2 g). δ (360 MHz, CDCl3) 1.35-1.42 (2H, m, CH2), 1.57-1.64 (2H, m, CH2), 2.00-2.40 (2H, m, CH2), 2.36 (2H, t, J=9.0 Hz, CH2), 3.15 (4H, m, t, J=7.0 Hz, 2 of CH2), 3.33 (6H, s, 2 of OMe), 4.35 (1H, t, J=5.7 Hz, CH).

Workup

  1. extractionthe mixture extracted with EtOAc (3×150 ml)
  2. washThe combined extracts were washed with H2O (3×50ml)
  3. dry with materialdried (Na2SO4)
  4. customevaporated
  5. distillationThe crude product was purified by distillation (1.2 g)

Sources & evidence

ORD record
ord-236248cb2e9f49cf85e4a869a7b084f4
Source dataset
uspto-grants-1996_10
Patent number
US05567726

Reaction notes

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