N-Hydroxyphthalimide → HCID 22131445, compound

HRID 1271788Notes

Reaction equation

HRID 1271788 reaction equation
[OH:1][CH2:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[N:33]1[C:37](=[O:38])[C:36]2=[CH:39][CH:40]=[CH:41][CH:42]=[C:35]2[C:34]1=[O:43].CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[CH:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:11]=[CH:12][C:3]=1[CH2:2][O:1][N:33]1[C:34](=[O:43])[C:35]2=[CH:42][CH:41]=[CH:40][CH:39]=[C:36]2[C:37]1=[O:38]

Participants

6

Reactant 4

HCID 10665N-HydroxyphthalimideHCID 11776TriphenylphosphineHCID 741282-NaphthalenemethanolHCID 5462977Diethyl azodicarboxylate

Product 1

HCID 22131445HCID 22131445, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(hydroxymethyl)napthalene (1.00 g, 6.33 mmol), triphenyl phosphine (1.73 g, 6.60 mmol, 1.04 equiv) and N-hydroxyphthalimide (1.08 g, 6.63 mmol, 1.05 equiv) were dissolved in 25 mL of dry THF. Diethylazodicarboxylate (1.09 mL, 6.93 mmol, 1.09 equiv) was then added dropwise and the reaction was stirred overnight. The reaction mixture was placed in a freezer for 2 h and then filtered, rinsing with Et2O, to give the proudct (1.38 g) as a white solid. MS(CI) m/e 321 (M+NH4)+.

Workup

  1. waitThe reaction mixture was placed in a freezer for 2 h
  2. filtrationfiltered
  3. washrinsing with Et2O
  4. customto give the proudct (1.38 g) as a white solid

Sources & evidence

ORD record
ord-35d285d871a9434084ff37dc755c8c67
Source dataset
uspto-grants-2007_04
Patent number
USRE039591E1

Reaction notes

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