Phthalimide → HCID 19605323, compound

HRID 1603635Notes

Reaction equation

HRID 1603635 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][CH2:10][CH2:11][C:12]#[C:13]O)[CH:5]=[CH:6][CH:7]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:34]1(=[O:44])[NH:38][C:37](=[O:39])[C:36]2=[CH:40][CH:41]=[CH:42][CH:43]=[C:35]12.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[C:34]1(=[O:44])[N:38]([C:13]#[C:12][CH2:11][CH2:10][CH2:9][CH2:8][C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=2)[C:37](=[O:39])[C:36]2=[CH:40][CH:41]=[CH:42][CH:43]=[C:35]12

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 19605228HCID 19605228, compound

Product 1

HCID 19605323HCID 19605323, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 6-(3-chlorophenyl)hexyn-1-ol (11.5 g, 55 mmol), triphenylphosphine (14.5 g, 55 mol) and phthalimide (8.1 g, 55 mol) in dry THF (110 ml) was treated with a solution of DEAD (9.6 g, 55 mmol) in THF (20 ml) over several minutes. After 16 h, volatiles were removed in vacuo and the residue treated with ether. The precipitated solid was removed, the filtrate evaporated and the residue purified by flash chromatography on silica using dichloromethane as eluant. Evaporation of the appropriate fractions gave the product as a solid (16.5 g, 89%)

Workup

  1. customvolatiles were removed in vacuo
  2. additionthe residue treated with ether
  3. customThe precipitated solid was removed
  4. customthe filtrate evaporated
  5. customthe residue purified by flash chromatography on silica
  6. customEvaporation of the appropriate fractions

Sources & evidence

ORD record
ord-babe85527bb84e7bb1d1ee44e482b8a5
Source dataset
uspto-grants-1999_11
Patent number
US05990102

Reaction notes

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