N-Hydroxyphthalimide → n-[3-[3-(2-Methoxyphenylsulfonyloxy)-5-methylphenoxy]propoxy]phthalimide

HRID 1977932Notes

Reaction equation

HRID 1977932 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[CH3:13][O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[S:21]([O:24][C:25]1[CH:26]=[C:27]([CH:33]=[C:34]([CH3:36])[CH:35]=1)[O:28][CH2:29][CH2:30][CH2:31][OH:32])(=[O:23])=[O:22].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[N:57]1[C:61](=[O:62])[C:60]2=[CH:63][CH:64]=[CH:65][CH:66]=[C:59]2[C:58]1=[O:67]>O1CCCC1>[CH3:13][O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[S:21]([O:24][C:25]1[CH:26]=[C:27]([CH:33]=[C:34]([CH3:36])[CH:35]=1)[O:28][CH2:29][CH2:30][CH2:31][O:32][N:57]1[C:58](=[O:67])[C:59]2=[CH:66][CH:65]=[CH:64][CH:63]=[C:60]2[C:61]1=[O:62])(=[O:23])=[O:22]

Participants

6

Reactant 4

HCID 10665N-HydroxyphthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 227224653-[3-(2-Methoxyphenylsulfonyloxy)-5-methylphenoxy]propanol

Product 1

HCID 22722658n-[3-[3-(2-Methoxyphenylsulfonyloxy)-5-methylphenoxy]propoxy]phthalimideYield 69%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Diethyl azodicarboxylate (67 (L, 0.40 mmol) was added dropwise over 5.5 min to 3-[3-(2-methoxyphenylsulfonyloxy)-5-methylphenoxy]propanol (118 mg, 0.33 mmol, prepared in the preceding step), triphenylphosphine (106 mg, 0.40 mmol), and N-hydroxyphthalimide (55 mg, 0.33 mmol) in anhydrous tetrahydrofuran (3 mL) at 0° C. under a nitrogen atmosphere. The solution was stirred at 0° C. for an additional 20 min then at ambient temperature overnight. The reaction mixture was concentrated, and the residue was purified by flash column chromatography (dichloromethane) to give the title compound (116 mg, 69%) as a colorless resin. 1H-NMR (300 MHz, CDCl3) (7.88-7.73 (m, 5H), 7.61 (ddd, 1H, J=8.4, 7.4, 1.7 Hz), 7.10 (d, 1H, J=8.4 Hz), 7.01 (dt, 1H, J=7.7, 0.9 Hz), 6.60 (br s, 1H), 6.56, (br s, 1H), 6.42 (t, 1H, J=2.2 Hz), 4.36 (t, 2H, J=6.2 Hz), 4.09 (t, 2H, J=6.2 Hz), 4.04 (s, 3H), 2.25 (s, 3H), 2.18 (pentet, 2H, J=6.2 Hz). Mass spectrum (MALDI-TOF, α-cyano-4-hydroxycinnamic acid matrix) calcd. for C25H23NO8S: 520.1 (M+Na). Found: 520.2.

Workup

  1. customat ambient temperature
  2. customovernight
  3. concentrationThe reaction mixture was concentrated
  4. customthe residue was purified by flash column chromatography (dichloromethane)

Sources & evidence

ORD record
ord-c75dbb161826451e97b0d41a499af7c1
Source dataset
uspto-grants-2001_05
Patent number
US06235778B1

Reaction notes

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