반응 #53455

반응 방정식

1-benzhydryl-3-[(3-methoxyphenyl)(methylsulfonyl)methylene]azetidine

→

1-benzhydryl-3-[(3-hydroxyphenyl)(methylsulfonyl)methylene]azetidine

수율 28.7%

용매

dichloromethane

dichloromethane

—

ice

반응 조건

후처리

1. 1
   세척The organic phase is washed with 3 times 50 cm3 of water
2. 2
   건조dried over magnesium sulfate
3. 3
   농축concentrated to dryness under reduced pressure (2.7 kPa)
4. 4
   기타The residue is precipitated in 150 cm3 of isopropyl ether
5. 5
   workup.DISSOLUTIONdissolved in 50 cm3 of dichloromethane
6. 6
   세척The organic phase is washed with 3 times 30 cm3 of a saturated aqueous solution of sodium bicarbonate
7. 7
   기타decanted off
8. 8
   건조dried over magnesium sulfate
9. 9
   농축concentrated to dryness under reduced pressure (2.7 kPa)
10. 10
    기타The residue is precipitated in 80 cm3 of ethyl ether

실험 절차

10 cm3 of a 1 M solution of boron tetrabromide in dichloromethane are added, with stirring, to a solution of 1.3 g of 1-benzhydryl-3-[(3-methoxyphenyl)(methylsulfonyl)methylene]azetidine in 100 cm3 of dichloromethane. The stirring is maintained for 16 hours at room temperature. The reaction medium is taken up in 100 cm3 of ice-cold water. The organic phase is washed with 3 times 50 cm3 of water, dried over magnesium sulfate and concentrated to dryness under reduced pressure (2.7 kPa). The residue is precipitated in 150 cm3 of isopropyl ether and then dissolved in 50 cm3 of dichloromethane. The organic phase is washed with 3 times 30 cm3 of a saturated aqueous solution of sodium bicarbonate, decanted off, dried over magnesium sulfate and concentrated to dryness under reduced pressure (2.7 kPa). The residue is precipitated in 80 cm3 of ethyl ether. 0.36 g of 1-benzhydryl-3-[(3-hydroxyphenyl)(methylsulfonyl)methylene]azetidine is obtained from a solid melting at 248° C. [NMR spectrum in DMSO-d6, T=300K, δ in ppm (300 MHz): 2.95 (3H, s, SCH3), 3.80 (2H, s, NCH2), 4.20 (2H, s, NCH2), 4.75 (1H, s, NCH), 6.85 (3H, m, 3 CH arom.), 7.25 (3H, m, 3 CH arom.), 7.35 (4H, t, J=7 Hz, 4CH arom.), 7.50 (4H, d, J=7 Hz, 4CH arom.), 9.50 (1H, s, OH)].

출처