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

HRID 1107151ノート

反応式

HRID 1107151 の反応式
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]

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 10992809Mercury(II) methanesulfonate触媒HCID 6212Chloroform溶媒HCID 6342Acetonitrile溶媒

反応条件

温度
48 °C

実験手順

(+)-(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).

後処理

  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)

出典と根拠

ORDレコード
ord-000dc22e19ea493bb91d95b8f4b494fe
出典データセット
uspto-grants-2000_05
特許番号
US06057369

反応ノート

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