Sodium Sulfite → 7-(Oxiran-2-yl)-3-(5-phenyl-4-(trifluoromethyl)isoxazol-3-yl)-4,5-dihydronaphtho[1,2-c]isoxazole

HRID 1506340Notes

Reaction equation

HRID 1506340 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]=[CH2:26])=[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.ClC1C=C(C=CC=1)C(OO)=[O:36].S([O-])([O-])=O.[Na+].[Na+]>ClCCl>[O:36]1[CH2:26][CH:25]1[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:29])([F:30])[F:28])=[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

Participants

5

Reactant 3

HCID 24437Sodium SulfiteHCID 70297m-Chloroperbenzoic acidHCID 671704243-(5-Phenyl-4-(trifluoromethyl)isoxazol-3-yl)-7-vinyl-4,5-dihydronaphtho[1,2-c]isoxazole

Product 1

HCID 866698787-(Oxiran-2-yl)-3-(5-phenyl-4-(trifluoromethyl)isoxazol-3-yl)-4,5-dihydronaphtho[1,2-c]isoxazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(5-phenyl-4-(trifluoromethyl)isoxazol-3-yl)-7-vinyl-4,5-dihydronaphtho[1,2-c]isoxazole (Preparation 6A, 0.09 g, 0.220 mmol) in dichloromethane (5 mL) was added 3-chlorobenzoperoxoic acid (0.109 g, 0.441 mmol) at room temperature. The reaction mixture was stirred at room temperature for 1.5 h. Next, 3 mL of 10% sodium sulfite solution was added to the reaction mixture at room temperature and the contents were stirred for 10 min. The reaction mixture was concentrated and partitioned between ethyl acetate (10 mL) and sat. aq. sodium bicarbonate (2×10 mL). The ethyl acetate layer was dried over sodium sulfate and concentrated to yield a pale yellow solid. LC/MS M+1=425.

Workup

  1. stirringthe contents were stirred for 10 min
  2. concentrationThe reaction mixture was concentrated
  3. custompartitioned between ethyl acetate (10 mL) and sat. aq. sodium bicarbonate (2×10 mL)
  4. dry with materialThe ethyl acetate layer was dried over sodium sulfate
  5. concentrationconcentrated
  6. customto yield a pale yellow solid

Sources & evidence

ORD record
ord-271f3407c9cb4d4ea36413d1074d1a82
Source dataset
uspto-grants-2015_12
Patent number
US09216972B2

Reaction notes

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