Oxirane, 2-[2-(phenylMethoxy)ethyl]- synthesis

8synthesis methods

Product Name:Oxirane, 2-[2-(phenylMethoxy)ethyl]-
CAS Number:94426-72-9
Molecular formula:C11H14O2
Molecular Weight:178.23

70388-33-9
16 suppliers
inquiry

94426-72-9
32 suppliers
$65.00/100mg

Yield:94426-72-9 97%

Reaction Conditions:

with 3-chloro-benzenecarboperoxoic acid in dichloromethane at 0 - 20; for 12 h;Inert atmosphere;

Steps:

(S)-2-(2-(benzyloxy)ethyl)oxirane (15):

To a cooled suspension of NaH (4.17 g, 60%, 0.104mol) in 40 mL dry THFwas added a solution of homoallylalcohol 10 (5 g, 0.069mol) in 10 mLTHF, and stirred for 10 minutes at same temperature, then BnBr was added (12.7 mL, 0.104 mol) followed by TBAIin catalytic amount. The reaction mass was stirred for next 4h at room temperature. After complete consumption ofstarting material, as indicated by TLC, reaction mass was quenched with saturated NH₄Cland extracted with ethyl acetate, the purification of crude product afforded the benzyl protectedolefin (10.8g, 96%) which was treated with m-CPBA (17.25 g, 0.1mol) in 80 mL DCM and stirredovernight at room temperature, the solvent was evaporated and excessof m-CPBA and m-chlorobenzoic acid was neutralised with saturated solution ofsodium bicarbonate and extracted with DCM, washed with brine, evaporation ofsolvent followed by purification on silica gel column chromatography afforded the epoxide (11.57 g,97%), which was resolutedwith (S,S)-jacabsen hydrolytic kinetic catalyst to afforded the compound 15 (5.8 g, 47%) as colorlessliquid; IR (KBr): 3456, 2924, 2860, 1722, 1490, 1453, 1257,1102, 1025, 743 cm^-1;[α]_D¹H NMR (500 MHz, CDCl₃): δ=7.29-7.34 (m, 5H), 4.51-4.52 (m, 2H), 3.58-3.64 (m, 2H), 3.05-3.09 (m,1H), 2.77 (dd, J= 4.12 Hz, 1H), 2.51(dd, J= 2.74 Hz, 1H), 1.87-1.94 (m,1H), 1.74-1.80 (m, 1H);¹³C NMR ( 75 MHz, CDCl₃):δ= 138.1,128.3, 127.4, 126.8, 73.0, 66.7, 50.0, 46.8, 32.8; MS (ESI): m/z = 179 [M+H]⁺, 201 [M+Na];HRMS (ESI): calcd for C₁₁H₁₄O₂Na [M+Na]⁺:201.0886; found: 201.0886.

References:

Dachavaram, Soma Shekar;Kalyankar, Kondbarao Balasaheb;Das, Saibal [Tetrahedron Letters,2014,vol. 55,# 41,p. 5629 - 5631] Location in patent:supporting information

19098-31-8
18 suppliers
inquiry

100-39-0
423 suppliers
$10.00/10g

94426-72-9
32 suppliers
$65.00/100mg

References

100-39-0
423 suppliers
$10.00/10g

94426-72-9
32 suppliers
$65.00/100mg

References

100-44-7 Synthesis

100-44-7
625 suppliers
$13.50/250G

94426-72-9
32 suppliers
$65.00/100mg

References

71998-69-1
1 suppliers
inquiry

94426-72-9
32 suppliers
$65.00/100mg

References