Hydrochloric Acid → HCID 86669941, compound

HRID 1506550Notes

Reaction equation

HRID 1506550 reaction equation
[C:1]1([C:7]2[O:11][N:10]=[C:9]([C:12]3[O:16][N:15]=[C:14]4[C:17]5[C:22]([CH2:23][CH2:24][C:13]=34)=[CH:21][C:20]([CH:25]=[O:26])=[CH:19][CH:18]=5)[C:8]=2[C:27]([F:30])([F:29])[F:28])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[Si]([C:35]#[N:36])(C)C.Cl.C(OCC)(=O)C>C(#N)C.[I-].[Zn+2].[I-]>[OH:26][CH:25]([C:20]1[CH:21]=[C:22]2[C:17](=[CH:18][CH:19]=1)[C:14]1=[N:15][O:16][C:12]([C:9]3[C:8]([C:27]([F:28])([F:29])[F:30])=[C:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[O:11][N:10]=3)=[C:13]1[CH2:24][CH2:23]2)[C:35]#[N:36]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 82115Trimethylsilyl cyanideHCID 866698753-(5-Phenyl-4-(trifluoromethyl)isoxazol-3-yl)-4,5-dihydronaphtho[1,2-c]isoxazole-7-carbaldehyde

Product 1

HCID 86669941HCID 86669941, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 9883512zinc(II)iodideCatalystHCID 6342AcetonitrileSolvent

Procedure

To 3-(5-phenyl-4-(trifluoromethyl)isoxazol-3-yl)-4,5-dihydronaphtho[1,2-c]isoxazole-7-carbaldehyde (Preparation 88A, 1 g, 2.4 mmol) in acetonitrile (75 mL) was added trimethylsilyl cyanide (0.49 mL, 3.7 mmol) and zinc iodide (0.79 g, 2.4 mmol). The reaction mixture was stirred for 70 min. at room temperature. After being cooled in ice-water bath, the mixture was acidified by addition of aqueous hydrochloric acid (1N, 4.4 mL, 4.4 mmol). Ethyl acetate (100 mL) was added and the layers were separated. The organic phase was washed with saturated sodium thiosulfate solution (5 mL×2). The organic phase was then dried, filtered, and concentrated to provide the product (±)-2-hydroxy-2-(3-(5-phenyl-4-(trifluoromethyl)isoxazol-3-yl)-4,5-dihydronaphtho[1,2-c]isoxazol-7-yl)acetonitrile (1.1 g, 2.4 mmol, 99% yield); LC/MS M+1=438.00; 1H NMR (400 MHz, CDCl3) δ ppm 8.09 (1H, d, J=7.92 Hz), 7.76 (2H, d, J=7.26 Hz), 7.50-7.68 (5H, m), 5.62 (1H, s), 3.11 (4H, s).

Workup

  1. customthe layers were separated
  2. washThe organic phase was washed with saturated sodium thiosulfate solution (5 mL×2)
  3. customThe organic phase was then dried
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-61392413fe0e4431bf0ca0dc06871306
Source dataset
uspto-grants-2015_12
Patent number
US09216972B2

Reaction notes

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