Water → 5-[2-(4-Chlorophenyl)-1,3-dioxolan-2-yl]-3-(3-methoxyphenyl)-2,1-benzisoxazole

HRID 852269Notes

Reaction equation

HRID 852269 reaction equation
[OH-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]([CH2:11][C:12]#N)[CH:8]=[CH:9][CH:10]=1.[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2([C:26]3[CH:31]=C[C:29]([N+:32]([O-])=[O:33])=[CH:28][CH:27]=3)[O:25][CH2:24][CH2:23][O:22]2)=[CH:17][CH:16]=1.O>CO>[Cl:14][C:15]1[CH:16]=[CH:17][C:18]([C:21]2([C:26]3[CH:27]=[CH:28][C:29]4[C:12]([CH:31]=3)=[C:11]([C:7]3[CH:8]=[CH:9][CH:10]=[C:5]([O:4][CH3:3])[CH:6]=3)[O:33][N:32]=4)[O:22][CH2:23][CH2:24][O:25]2)=[CH:19][CH:20]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 88310(3-Methoxyphenyl)acetonitrileHCID 154896262-(4-Chlorophenyl)-2-(4-nitrophenyl)-1,3-dioxolane

Product 1

HCID 227143745-[2-(4-Chlorophenyl)-1,3-dioxolan-2-yl]-3-(3-methoxyphenyl)-2,1-benzisoxazoleYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium hydroxide (16.4 g) and (3-methoxyphenyl)acetonitrile (20.6 ml) were added at room temperature to a solution of interm. (5-a) (25 g) in methanol (100 ml) and the mixture was stirred at room temperature overnight. Water was added, the precipitate was filtered off, washed with cold methanol and dried. The product was used without further purification, yielding 30 g (90%) of 5-[2-(4-chlorophenyl)-1,3-dioxolan-2-yl]-3-(3-methoxyphenyl)-2,1-benzisoxazole (interm. 5-b).

Workup

  1. filtrationthe precipitate was filtered off
  2. washwashed with cold methanol
  3. customdried
  4. customThe product was used without further purification

Sources & evidence

ORD record
ord-84872167a9cd45d8a236c0e81082e405
Source dataset
uspto-grants-2007_08
Patent number
US07253183B2

Reaction notes

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