Hydrochloric Acid → HCID 86669938, compound

HRID 1506545Notes

Reaction equation

HRID 1506545 reaction equation
[CH2:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:14][N:13]=[C:12]3[C:15]4[C:20]([CH2:21][CH2:22][C:11]=23)=[CH:19][C:18]([CH:23]=[O:24])=[CH:17][CH:16]=4)=[CH:6][CH:5]=1)[CH2:2][CH3:3].C[Si]([C:29]#[N:30])(C)C.Cl>ClCCl.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[OH:24][CH:23]([C:18]1[CH:19]=[C:20]2[C:15](=[CH:16][CH:17]=1)[C:12]1=[N:13][O:14][C:10]([C:7]3[CH:8]=[CH:9][C:4]([CH2:1][CH2:2][CH3:3])=[CH:5][CH:6]=3)=[C:11]1[CH2:22][CH2:21]2)[C:29]#[N:30]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 82115Trimethylsilyl cyanideHCID 86669939HCID 86669939, compound

Product 1

HCID 86669938HCID 86669938, compoundYield 98.7%

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3-(4-propylphenyl)-4,5-dihydronaphtho[1,2-c]isoxazole-7-carbaldehyde (Preparation 11C, 250 mg, 0.78 mmol) in dichloromethane (4 mL) at 0° C. was added trimethylsilyl cyanide (0.13 mL, 0.94 mmol) and titanium(IV) isopropoxide (0.46 mL, 1.6 mmol). The reaction mixture was stirred for 1 h before 1 N HCl (aq) was added along with additional dichloromethane. The organic layer was dried (over magnesium sulfate), filtered, and concentrated to give crude 2-hydroxy-2-(3-(4-propylphenyl)-4,5-dihydronaphtho[1,2-c]isoxazol-7-yl)acetonitrile (Preparation 127A, 265 mg, 0.77 mmol, 98% yield): LC/MS M+1=345.1.

Workup

  1. dry with materialThe organic layer was dried (over magnesium sulfate)
  2. filtrationfiltered
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-97178c0e0ad34f329ee74c99408c514c
Source dataset
uspto-grants-2015_12
Patent number
US09216972B2

Reaction notes

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