Hexamethylphosphoramide → HCID 70457121, compound

HRID 1719200Notes

Reaction equation

HRID 1719200 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° C.

Workup

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

Sources & evidence

ORD record
ord-3c7ad9bc7c194b2f974d4ce4202b4674
Source dataset
uspto-grants-1985_09
Patent number
US04539319

Reaction notes

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