Methyl 3-Hydroxybenzoate → 3-Phenoxy-4,5-dihydroisoxazole

HRID 1746136Notes

Reaction equation

HRID 1746136 reaction equation
Br[C:2]1[CH2:6][CH2:5][O:4][N:3]=1.COC(=O)[C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([OH:16])[CH:11]=1>>[O:16]([C:2]1[CH2:6][CH2:5][O:4][N:3]=1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:10][CH:11]=1

Participants

3

Reactant 2

HCID 88068Methyl 3-HydroxybenzoateHCID 219834983-Bromo-4,5-dihydroisoxazole

Product 1

HCID 149604673-Phenoxy-4,5-dihydroisoxazole

Procedure

3-phenoxy-4,5-dihydroisoxazole I-176a and I-176b were prepared in 2 steps from racemic compound I-14. Bromo-4,5-dihydroisoxazole I-14 was reacted with 3-hydroxybenzoic acid methyl ester using Method 5 followed by hydroysis using the analogous conditions as in example 94. [M+H]+=368.0 m/z. Activity: C

Sources & evidence

ORD record
ord-41d7763487704e29b6673e37e80724f6
Source dataset
uspto-grants-2015_10
Patent number
US09149465B2

Reaction notes

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