Sodium Cyanide → 7-Cyano-1-(2-furyl)-1-methoxy-3-heptyne

HRID 1032508Notes

Reaction equation

HRID 1032508 reaction equation
Cl[CH2:2][CH2:3][CH2:4][C:5]#[C:6][CH2:7][CH:8]([C:11]1[O:12][CH:13]=[CH:14][CH:15]=1)[O:9][CH3:10].[C-:16]#[N:17].[Na+]>CN(C)P(=O)(N(C)C)N(C)C>[C:16]([CH2:2][CH2:3][CH2:4][C:5]#[C:6][CH2:7][CH:8]([C:11]1[O:12][CH:13]=[CH:14][CH:15]=1)[O:9][CH3:10])#[N:17]

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 147744247-Chloro-1-(2-furyl)-1-methoxy-3-heptyne

Product 1

HCID 221661397-Cyano-1-(2-furyl)-1-methoxy-3-heptyneYield 88.1%

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Conditions

Temperature
25 °C

Procedure

A stirred mixture of 0.45 g of 7-chloro-1-(2-furyl)-1-methoxy-3-heptyne, 0.20 g of sodium cyanide, and 4.0 ml of hexamethylphosphoric triamide was maintained at 25° C. for 22 hours. The mixture was partitioned with water and 1:1 hexaneether. The organic layer was washed with water and brine, dried and concentrated. The resulting oil was distilled at 0.30 mm on a Kugelrohr at 105°-110° C., giving 0.38 g of the desired compound as an oil; PMR δ 2.36 (2H, t, CH2CN).

Workup

  1. customThe mixture was partitioned with water and 1:1 hexaneether
  2. washThe organic layer was washed with water and brine
  3. customdried
  4. concentrationconcentrated
  5. distillationThe resulting oil was distilled at 0.30 mm on a Kugelrohr at 105°-110° C.

Sources & evidence

ORD record
ord-3457431b8b0645e9b955bb84ceb4f590
Source dataset
uspto-grants-1990_09
Patent number
US04958037

Reaction notes

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