2-Methyl-5-hydroxypyridine → 2-Methyl-5-[(oxiran-2-yl)methoxy]pyridine

HRID 1061276Notes

Reaction equation

HRID 1061276 reaction equation
[CH3:1][C:2]1[N:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[N+](C1C=C(S(O[CH2:22][C@@H:23]2[CH2:25][O:24]2)(=O)=O)C=CC=1)([O-])=O>>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][CH2:22][CH:23]2[CH2:25][O:24]2)=[CH:6][N:7]=1

Participants

3

Reactant 2

HCID 142752-Methyl-5-hydroxypyridineHCID 146490Benzenesulfonic acid, 3-nitro-, (2S)-2-oxiranylmethyl ester

Product 1

HCID 222202352-Methyl-5-[(oxiran-2-yl)methoxy]pyridine

Procedure

The title compound was prepared from 6-methyl-3-pyridinol and (2S)-oxiranylmethyl 3-nitrobenzenesulfonate in substantially the same manner as described in Example 123. The product was obtained as a brown oil; 1H NMR (400 MHz, DMSO-d6) δ 2.38 (s, 2.38, 1H), 2.68-2.70 (m, 1H), 2.81-2.84 (m, 1H), 3.30-3.34 (m, 1H), 3.83-3.87 (m, 1H), 4.34-4.38 (m, 1H), 7.15-7.17 (m, 1H), 7.28-7.31 (m, 1H), 8.15-8.16m (m, 1H); MS (ES) m/z: 165 (M)+.

Workup

  1. customThe product was obtained as a brown oil

Sources & evidence

ORD record
ord-e32c9b1068e446baaecdc8a038f7c268
Source dataset
uspto-grants-2003_02
Patent number
US06525202B2

Reaction notes

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