Triphenylphosphine → (3S,4R)-3-methyl-4-(4-phenylbutyl)oxetan-2-one

HRID 1107151노트

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HRID 1107151 반응식
O[C@H:2]([CH2:8][CH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C@H:3]([CH3:7])[C:4]([OH:6])=[O:5].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1C=C(SSC2N=CC=CC=2)N=CC=1>C(Cl)(Cl)Cl.C(#N)C.CS([O-])(=O)=O.[Hg+2].CS([O-])(=O)=O>[CH3:7][C@H:3]1[C@@H:2]([CH2:8][CH2:9][CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[O:5][C:4]1=[O:6]

참가 물질

7

반응물 3

HCID 11776TriphenylphosphineHCID 650932,2'-Dipyridyl disulfideHCID 57188911(+)-(2S, 3R)-3-hydroxy-2-methyl-7-phenylheptanoic acid

생성물 1

HCID 57048705(3S,4R)-3-methyl-4-(4-phenylbutyl)oxetan-2-one수율 66%

시약·촉매·용매 3

HCID 10992809Mercury(II) methanesulfonate촉매HCID 6212Chloroform용매HCID 6342Acetonitrile용매

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온도
48 °C

실험 절차

(+)-(2S, 3R)-3-Hydroxy-2-methyl-7-phenylheptanoic acid is added to a solution of triphenylphosphine (0.88 g, 3.4 mmol) and 2,2'-dipyridyl disulfide (0.7 g, 3.2 mmol) in chloroform (20 mL) and is stirred for 20 minutes. Mercury(II) methanesulfonate (1.6 g, 4.2 mmol) is suspended in acetonitrile (52 mL), warmed to 48° C. and the activated ester/chloroform solution is added over 5 minutes. This mixture is heated for 1 minute after completion of the addition and then cooled. The mixture is filtered through Celite, the filtrate concentrated in vacuo and the residue is purified by column chromatography (silica, 25% ether in petroleum ether) to yield (3S,4R)-3-methyl-4-(4-phenylbutyl)oxetan-2-one (0.3 g, 66%). 1H NMR (300 MHz, CDCl3) δ 7.31-7.26 (m, 2H), 7.21-7.15 (m, 3H), 4.19-4.13 (m, 1H), 3.25-3.16 (m, 1H), 2.64 (t, J=7.6 Hz, 2H), 1.95-1.64 (m, 4H), 1.55-1.40 (m, 5H), 1.37 (d, J=7.5 Hz, 3H).

후처리

  1. temperatureThis mixture is heated for 1 minute
  2. additionafter completion of the addition
  3. temperaturecooled
  4. filtrationThe mixture is filtered through Celite
  5. concentrationthe filtrate concentrated in vacuo
  6. customthe residue is purified by column chromatography (silica, 25% ether in petroleum ether)

출처 및 근거

ORD 기록
ord-000dc22e19ea493bb91d95b8f4b494fe
출처 데이터셋
uspto-grants-2000_05
특허 번호
US06057369

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