Ethanol → (2R-trans)-(2-naphthalenyl) 3-[2-(8-phenyloctyl)phenyl]oxiranecarboxylate

HRID 248231

反応式

HRID 248231 の反応式
[CH:1](=[O:4])[CH:2]=[CH2:3].[Na].[C:6]1([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]2[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=2[CH:22]=[O:23])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.CC([C:31]1[CH:40]=[CH:39]C2[C:33](=[CH:34][CH:35]=CC=2)[CH:32]=1)=O.[CH2:41]([OH:43])[CH3:42]>>[C:6]1([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]2[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=2[C@@H:22]2[O:23][C@H:42]2[C:41]([O:4][C:1]2[CH:35]=[CH:34][C:33]3[C:3](=[CH:39][CH:40]=[CH:31][CH:32]=3)[CH:2]=2)=[O:43])[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

参加物

6

反応物 5

HCID 702EthanolHCID 71222-AcetylnaphthaleneHCID 7847AcroleinHCID 5360545Sodium2 回HCID 98176132-(8-Phenyloctyl)benzaldehyde

生成物 1

HCID 11145251(2R-trans)-(2-naphthalenyl) 3-[2-(8-phenyloctyl)phenyl]oxiranecarboxylate

反応条件

温度
10 °C

実験手順

Preparation of (E)-1-(2-naphthalenyl)-3-2-(8-phenyloctyl)phenyl]-2-propen-1-one. To a cooled (5° C.) solution of ethanol (95%, 3.53 L) in a 12 L 3 -neck flask, under nitrogen, was added sodium metal (36.8 g, 1.16 mol) over a period of 30 min. After the sodium had dissolved, stirring was continued for 5 min, and 2-(8phenyloctyl)benzaldehyde (200 g, 0.68 mol) was added. The reaction was cooled to 10° C. and 2-acetonaphthone (115.6 g, 0.679 mol) was added in one portion. The reaction was seeded with the desired product (2 g) and stirred for 18 h at ambient temperature. A yellow precipitate was present after that time. The reaction was treated with ice water (350 mL), cooled to 10° C., and filtered. The filter cake was washed with 50% aqueous ethanol (400 mL). The product, a yellow solid, was air dried and any lumps were pulverized. The product was dried at 25° C. (0.1 mm Hg) for 24 h to yield 248 g (89%): mp 41.0-42.5° C.; IR (KBr) 1658, 1597, 1467, 1325, 1185, 1124, 1016, 970, 763 cm-1; 1H NMR (CDCl3, 360 MHz) δ8.55 (d, 1 H, naphthyl-1H, J=1.2 Hz), 8 21 (d, 1 H, J=15.5 Hz, olefinic proton), 7.12-8.11 (m, 15 H), 7.62 (d, 1 H, J=15.6 Hz), 2.75 (t, 2 H, J=7.71 Hz), 2.57 (t, 2 H, J=7.71 Hz), 1.59 (b, 4 H), 1.29 (b, 8 H); 13C NMR (CDCl3) δ190.25, 143.31, 142.86, 142.40, 135.59, 135.46, 133 47, 132.57, 130.21, 130 15, 129.91, 129.47, 128.52, 128.34, 128.15, 127.79, 126.72, 126.58, 126.31, 125.47, 124.49, 123.34, 35.91, 33.39, 31.72, 31.42, 29.41, 29.38, 29.34, 29.23; TLC Rf 0.55 (CH2Cl2 :n-hexane, 3:1., Silica gel GF); HPLC RT 17.7 min (Waters μ-Bondapak®C-18; 30 cm×3.9 mm; CH3CN:water, 85:15; 1.5 ml/min; UV detection at 230 nm). Anal. Calcd for C33H34O: C, 88.74; H, 7.67. Found: C, 88.84; H, 7.68.

出典と根拠

ORDレコード
ord-f5d73baed31b4c2c92758de780c4c721
出典データセット
uspto-grants-1993_05
特許番号
US05208353

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