Water → Methyl 7-phthalimidohept-5-ynoate

HRID 358618Notes

Reaction equation

HRID 358618 reaction equation
[C:1]1(=[O:11])[NH:5][C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[K].Br[CH2:14][C:15]#[C:16][CH2:17][CH2:18][CH2:19][C:20]([O:22][CH3:23])=[O:21].O>CN(C)C=O>[C:1]1(=[O:11])[N:5]([CH2:14][C:15]#[C:16][CH2:17][CH2:18][CH2:19][C:20]([O:22][CH3:23])=[O:21])[C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12

Participants

5

Reactant 3

HCID 962WaterHCID 11287432Methyl 7-bromohept-5-ynoateHCID 24194345Phthalimide potassium salt

Product 1

HCID 20066955Methyl 7-phthalimidohept-5-ynoateYield 44.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture or potassium phthalimide (2.31 g) and methyl 7-bromohept-5-ynoate (3.0 g) in dimethylformamide (35 ml) was heated at 110° C. for 4.5 hours. The cooled solution was poured into water (75 ml) and the pH of the solution was adjusted to 6. The resulting solution was extracted with ether (4×200 ml) and the combined ether extracts were dried over magnesium sulphate, the solvent was removed and the residue was chromatographed on silica gel eluted with chloroform to give the title compound (1.56 g) m.p. 62°-63° C.

Workup

  1. extractionThe resulting solution was extracted with ether (4×200 ml)
  2. dry with materialthe combined ether extracts were dried over magnesium sulphate
  3. customthe solvent was removed
  4. customthe residue was chromatographed on silica gel
  5. washeluted with chloroform

Sources & evidence

ORD record
ord-c47cfd8ad65b48ce8bb0d9166b2d69ef
Source dataset
uspto-grants-1991_03
Patent number
US04997847

Reaction notes

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