m-Chloroperbenzoic acid → HCID 86650543, compound

HRID 2066641Notes

Reaction equation

HRID 2066641 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][O:16][CH2:17][C:18]([CH3:20])=[CH2:19])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC1C=CC=C(C(OO)=[O:29])C=1>>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][O:16][CH2:17][C:18]2([CH3:20])[CH2:19][O:29]2)=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 10707028HCID 10707028, compound

Product 1

HCID 86650543HCID 86650543, compoundYield 95%

Procedure

Epoxidation of alkene 122 with 3-chloroperbenzoic acid as in Example 2G for 2.5 h, followed by chromatography of the product on silica gel, eluting with 50% CH2Cl2/petroleum ether (foreruns) and then with 50-80% CH2Cl2/petroleum ether and CH2Cl2, gave 2-({[4-(benzyloxy)benzyl]oxy}methyl)-2-methyloxirane (124) (95%) as an oil: 1H NMR (CDCl3) δ 7.45-7.29 (m, 5H), 7.26 (dt, J=8.7, 2.4 Hz, 2H), 6.95 (dt, J=8.7, 2.5 Hz, 2H), 5.07 (s, 2H), 4.52 (d, J=11.6 Hz, 1H), 4.47 (d, J=11.6 Hz, 1H), 3.54 (d, J=11.0 Hz, 1H), 3.42 (d, J=11.0 Hz, 1H), 2.73 (d, J=4.9 Hz, 1H), 2.62 (d, J=4.9 Hz, 1H), 1.39 (s, 3H); HREIMS calcd for C18H20O3 m/z (M+) 284.1412. found 284.1416.

Workup

  1. washeluting with 50% CH2Cl2/petroleum ether (foreruns)

Sources & evidence

ORD record
ord-acf28e9de89a43ffa2c2f92ee2bf4aa8
Source dataset
uspto-grants-2012_10
Patent number
US08293734B2

Reaction notes

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