Triphenylphosphine → HCID 59497686, compound

HRID 1747315Notes

Reaction equation

HRID 1747315 reaction equation
[C:1]([N:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[NH:6][C:5]1=[O:13])([CH3:3])=[CH2:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:33]1([CH2:43]O)[C:42]2[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=2)[CH:36]=[CH:35][CH:34]=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[C:1]([N:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]([CH2:43][C:33]2[C:42]3[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=3)[CH:36]=[CH:35][CH:34]=2)[C:5]1=[O:13])([CH3:3])=[CH2:2]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 209081-NaphthalenemethanolHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 1002781,3-Dihydro-1-(1-methylvinyl)-2H-benzimidazol-2-one

Product 1

HCID 59497686HCID 59497686, compoundYield 89.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-isopropenylbenzimidazolone (1.0 g, 5.7 mmol) in dry THF (80 mL) are added triphenylphosphine (1.8 g, 6.9 mmol) and naphthalen-1-yl-methanol (1.1 g, 6.9 mmol). Then diisopropyl azodicarboxylate (1.4 mL, 6.9 mmol) is added drop wise into the above solution at room temperature. The mixture is stirred for 16 hrs and then the solvent is removed under vacuum. The residue is purified by flash column chromatography using 10% EtOAc in hexanes to give 1.6 g (89%) of 1-isopropenyl-3-naphthalen-1-ylmethyl-1,3-dihydro-benzimidazol-2-one.

Workup

  1. customthe solvent is removed under vacuum
  2. customThe residue is purified by flash column chromatography

Sources & evidence

ORD record
ord-deddd4b417684acc9696749a9bb571b1
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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