Water → HCID 18973848, compound

HRID 2395004Notes

Reaction equation

HRID 2395004 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12](Br)=[CH:11][C:10]=1[CH2:16][CH2:17][CH2:18][C:19]1[CH:28]=[CH:27][C:22]([C:23]([O:25][CH3:26])=[O:24])=[CH:21][CH:20]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:29]([Cu])#[N:30].C(N)CN.O>CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:29]#[N:30])=[CH:11][C:10]=1[CH2:16][CH2:17][CH2:18][C:19]1[CH:28]=[CH:27][C:22]([C:23]([O:25][CH3:26])=[O:24])=[CH:21][CH:20]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 3301EthylenediamineHCID 18973795HCID 18973795, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 18973848HCID 18973848, compoundYield 66.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of methyl 4-[3-(2-benzyloxy-5-bromophenyl)propyl]-benzoate (0.5 g) and CuCN (250 mg) in DMF (20 ml) was heated at reflux for 18 hours, poured into ethylene diamine (20 ml) and water (60 ml) and extracted with ethyl acetate (3×100 ml). The combined extracts were washed with brine (100 ml), dried (magnesium sulphate), filtered and evaporated to give methyl 4-[3-(2-benzyloxy-5-cyanophenyl)propyl]-benzoate (290 mg).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 18 hours
  3. extractionextracted with ethyl acetate (3×100 ml)
  4. washThe combined extracts were washed with brine (100 ml)
  5. dry with materialdried (magnesium sulphate)
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-d50471bb75f74aa798450293b1097dc4
Source dataset
uspto-grants-1998_09
Patent number
US05811459

Reaction notes

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