Sodium Cyanide → 2-(3-(Hydroxymethyl)oxetan-3-yl)acetonitrile
Reaction equation
Br[CH2:2][C:3]1([CH2:7][OH:8])[CH2:6][O:5][CH2:4]1.[C-:9]#[N:10].[Na+]>C(O)C>[OH:8][CH2:7][C:3]1([CH2:2][C:9]#[N:10])[CH2:6][O:5][CH2:4]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 42 g (0.23 mol) of [3-(bromomethyl)oxetan-3-yl] methanol (produced according to Example 1) in 420 ml of ethanol was refluxed with 13 g (0.265 mol) of sodium cyanide for 18 hours. After cooling to room temperature, the precipitated sodium bromide was filtered off and the filtrate concentrated by evaporation. The residue was distilled at 0.4 torr. The yield of product as a colorless oil was 16 g (54 percent). The boiling point of the product was 107° C./0.4 torr. Other data concerning the product was:
Workup
- filtrationthe precipitated sodium bromide was filtered off
- concentrationthe filtrate concentrated by evaporation
- distillationThe residue was distilled at 0.4 torr
- customwas 107° C.
Sources & evidence
- ORD record
- ord-3fcf3ec291cc42e19566979fd5a4612d
- Source dataset
- uspto-grants-1996_01
- Patent number
- US05486622
Reaction notes
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