Succinimide → 7-Nitroisochroman

HRID 488372Notes

Reaction equation

HRID 488372 reaction equation
O[CH2:2][C:3]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:4]=1[CH2:12][CH2:13][OH:14].C1(=O)NC(=O)CC1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[N+:9]([C:7]1[CH:6]=[CH:5][C:4]2[CH2:12][CH2:13][O:14][CH2:2][C:3]=2[CH:8]=1)([O-:11])=[O:10]

Participants

6

Reactant 4

HCID 11439SuccinimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 222696612-(2-(Hydroxymethyl)-4-nitrophenyl)ethanol

Product 1

HCID 9017397-NitroisochromanYield 66.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 2-[2-(hydroxymethyl)-4-nitrophenyl]ethanol (Step 1, 1.65 g, 8.37 mmol), succinimide (829 mg, 8.37 mmol) and triphenylphosphine (2.46 g, 9.37 mmol) in dry THF at 0° C. under N2 is treated with diethyl azodicarboxylate (1.50 mL, 9.54 mmol) dropwise over 5 mins, and the resulting mixture is stirred at 0° C. for 4 hrs and then concentrated under reduced pressure. The residue is chromatographed on a Flash 40M silica gel (90 g, 32-63 μm) cartridge, eluting with EtOAc/heptane (10/90), and those fractions with an Rf=0.60 by TLC (EtOAc/hexane, 50/50) are pooled and concentrated to give 995 mg (66%) of the title compound as a white solid, mp 96-98° C.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue is chromatographed on a Flash 40M silica gel (90 g, 32-63 μm) cartridge
  3. washeluting with EtOAc/heptane (10/90)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c24b3483cc30442e9feb8389705b48eb
Source dataset
uspto-grants-2005_12
Patent number
US06972286B2

Reaction notes

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