Hexamethylphosphoramide → HCID 70457121, compound

HRID 1981854Notes

Reaction equation

HRID 1981854 reaction equation
[CH2:1]([O:8][C:9]1[C:18]2[CH2:17][CH2:16][CH2:15][CH2:14][C:13]=2[C:12](Br)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:20][N:21](C)P(N(C)C)(N(C)C)=O>C(Cl)Cl>[CH2:1]([O:8][C:9]1([C:20]#[N:21])[C:18]2[CH2:17][CH2:16][CH2:15][CH2:14][C:13]=2[CH:12]=[CH:11][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 12679HexamethylphosphoramideHCID 15524285HCID 15524285, compound

Product 1

HCID 70457121HCID 70457121, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-Benzyloxy-4-bromo-5,6,7,8-tetrahydronaphthalene (4.5 g, 14.2 mM), cuprous cyanide (1.71 g, 8.67 mM) pyridine (1 ml) and hexamethylphosphoramide (0.25 ml) was stirred at 170° C. for 16 hours. The resultant viscous mixture was dissolved in methylene chloride and washed with ammonium hydroxide solution, saturated brine solution, dried (sodium sulphate) and evaporated to give an oil (4.6 g). This oil was chromatographed on alumina (eluted with methylene chloride:petroleum ether, 1:1) to give the nitrile (5) as a solid (2.4 g) m pt 74°-75.5° C.

Workup

  1. washwashed with ammonium hydroxide solution, saturated brine solution
  2. dry with materialdried (sodium sulphate)
  3. customevaporated

Sources & evidence

ORD record
ord-c28907bf6b274ed28abffd07f645ae28
Source dataset
uspto-grants-1986_06
Patent number
US04594195

Reaction notes

Loading…