반응 #62576

반응 방정식

n-butyllithium

Compound 1

1-Hexadecyloxy-3-triphenylmethoxypropan-2-one

Water

→

title compound ( 2 )

수율 82.0%

3-Hexadecyloxy-3-(triphenylmethoxymethyl)-1-propene

수율 82.0%

용매

hexane

dioxane

dioxane

반응 조건

후처리

1. 1
   workup.STIRRINGthe mixture was stirred for 2 hours
2. 2
   기타the solution was partitioned between hexane and water
3. 3
   세척The aqueous layer was washed 2 times with hexane
4. 4
   건조the combined organic layers were dried over Na2SO4
5. 5
   농축concentrated
6. 6
   기타The residue was crystallized from ethanol

실험 절차

A solution of n-butyllithium (47 ml, 113 mmol) in hexane was added to a suspension of methyltriphenylphosphonium bromide (40.0 g, 112 mmol) in 100 ml dry dioxane under N2 and the dark red solution was stirred at room temperature for 45 minutes. Compound 1 (35.1 g, 63.1 mmol) in 100 ml dry dioxane was added and the mixture was stirred for 2 hours. Water (10 ml) was added and the solution was partitioned between hexane and water. The aqueous layer was washed 2 times with hexane and the combined organic layers were dried over Na2SO4 and concentrated. The residue was crystallized from ethanol to afford 28.8 g (82%) of the title compound (2) as white needles, m.p. 34° ; NMR (CDCl3, (CH3)4Si); δ0.90 (t, 3H, J=6 Hz, --CH3), 1.25 (s, 26H, --CH2 --), 1.62 (m, 2H, --OCH2CH2R), 3.35 (t, 2H, J=7 Hz, --OCH2R), 3.62 (s, 2H, CH2OTr), 3.96 (s, 2 H, --CH2OR), 5.20 (d, 1 H, J=2 Hz, olefin), 5.40 (d, 1H, J=2 Hz, olefin), 7.2-7.5 (m, 15H, C(C6H5)85)3).

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