N-Hydroxyphthalimide → HCID 23353087, compound

HRID 234875Notes

Reaction equation

HRID 234875 reaction equation
[OH:1][N:2]1[C:6](=[O:7])[C:5]2=[CH:8][CH:9]=[CH:10][CH:11]=[C:4]2[C:3]1=[O:12].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[CH2:33][CH2:34][CH2:35][C:36]#[C:37][C:38]1[CH:43]=[CH:42][C:41]([F:44])=[CH:40][CH:39]=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[F:44][C:41]1[CH:42]=[CH:43][C:38]([C:37]#[C:36][CH2:35][CH2:34][CH2:33][O:1][N:2]2[C:3](=[O:12])[C:4]3=[CH:11][CH:10]=[CH:9][CH:8]=[C:5]3[C:6]2=[O:7])=[CH:39][CH:40]=1

Participants

6

Reactant 4

HCID 10665N-HydroxyphthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 189879965-(4-Fluorophenyl)-4-pentyn-1-ol

Product 1

HCID 23353087HCID 23353087, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

33.4 g (0.205 mol) of N-hydroxyphthalimide and 53.8 g (0.205 mol) of triphenylphosphine were added to a solution of 33.1 g (0.186 mol) of 5-hydroxy-1-(4-fluorophenyl)-1-pentine in 430 ml of tetrahydrofuran. 35.7 g (0.205 mol) of diethyl azodicarboxylate were then added in the course of 2.5 hours with monitoring of the temperature (max. 40° C.). Stirring was carried out overnight at room temperature, the mixture was evaporated down under reduced pressure and the residue was taken up with 300 ml of dichloromethane. The solution was washed twice with sodium carbonate solution and once with saturated sodium chloride solution. After drying and evaporating down, the crude product was purified by chromategraphy over silica gel. The eluent used was initially dichloromethane/n-hexane and subsequently pure dichloromethane. Yield: 82%; mp.: 85°-88° C.

Workup

  1. customthe mixture was evaporated down under reduced pressure
  2. washThe solution was washed twice with sodium carbonate solution and once with saturated sodium chloride solution
  3. customAfter drying
  4. customevaporating down
  5. customthe crude product was purified by chromategraphy over silica gel

Sources & evidence

ORD record
ord-62a8d454f04d406ba642f72182331167
Source dataset
uspto-grants-1997_01
Patent number
US05597776

Reaction notes

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