N-Hydroxyphthalimide → HCID 22633846, compound

HRID 1369317Notes

Reaction equation

HRID 1369317 reaction equation
[CH2:1]([OH:7])[CH2:2][CH2:3][CH2:4][C:5]#[CH:6].O[N:9]1[C:13](=[O:14])[C:12]2=[CH:15][CH:16]=[CH:17][CH:18]=[C:11]2[C:10]1=[O:19]>C1COCC1>[C:13]1(=[O:14])[N:9]([O:7][CH2:1][CH2:2][CH2:3][CH2:4][C:5]#[CH:6])[C:10](=[O:19])[C:11]2=[CH:18][CH:17]=[CH:16][CH:15]=[C:12]12

Participants

4

Reactant 2

HCID 10665N-HydroxyphthalimideHCID 702345-Hexyn-1-ol

Product 1

HCID 22633846HCID 22633846, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 5-Hexyn-1-ol is added N-hydroxyphthalimide (1.1 equivalent) in dry THF. To this mixture is added diethylazo-dicarboxylate (DEAD) dropwise with stirring at ambient temperature for 18 hours. Evaporation of the reaction mixture followed by silica column purification yielded the 1-phthalimidooxy-hex-5-yne.

Workup

  1. customEvaporation of the reaction mixture
  2. customfollowed by silica column purification

Sources & evidence

ORD record
ord-2de380f24fc34dcf81487f2ced65901c
Source dataset
uspto-grants-2003_06
Patent number
US06576752B1

Reaction notes

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