(+)-17beta-Tert.butoxy-13beta-ethyl-3-methoxygona-1,3,5(10),9(11)-tetraene → (+)-17beta-Tert.butoxy-13 beta-ethyl-3-methoxygona-1,3,5(10)-triene

HRID 1580750ノート

反応式

HRID 1580750 の反応式
[C:1]([O:5][C@@H:6]1[C@:14]2([CH2:15][CH3:16])[C@H:9]([C@@H:10]3[CH2:24][CH2:23][C:22]4[CH:21]=[C:20]([O:25][CH3:26])[CH:19]=[CH:18][C:17]=4[C:11]3=[CH:12][CH2:13]2)[CH2:8][CH2:7]1)([CH3:4])([CH3:3])[CH3:2].[H][H]>[Pd].C(OCC)(=O)C>[C:1]([O:5][C@@H:6]1[C@:14]2([CH2:15][CH3:16])[C@H:9]([C@@H:10]3[CH2:24][CH2:23][C:22]4[CH:21]=[C:20]([O:25][CH3:26])[CH:19]=[CH:18][C:17]=4[C@H:11]3[CH2:12][CH2:13]2)[CH2:8][CH2:7]1)([CH3:4])([CH3:2])[CH3:3]

参加物

5

反応物 2

HCID 18595371(+)-17beta-Tert.butoxy-13beta-ethyl-3-methoxygona-1,3,5(10),9(11)-tetraeneHCID 178418361HCID 178418361、化合物2 回

生成物 1

HCID 18595372(+)-17beta-Tert.butoxy-13 beta-ethyl-3-methoxygona-1,3,5(10)-triene収率 122.3%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 8857Ethyl Acetate溶媒

実験手順

A mixture of lg (2.82 mmoles) of (+)-17β-tert.butoxy- 13β-ethyl-3-methoxygona-1,3,5(10),9(11)-tetraene, 0.25 g of 5% palladium on carbon and 25 ml of ethyl acetate was stirred in an atmosphere of hydrogen for 1 hr during which time a total of 74 ml of hydrogen was absorbed (70.5 ml theory). The catalyst was filtered with suction on Celite and the filter cake was washed well with ethyl acetate. Concentration of the combined filtrate and washes in vacuo gave 1.23 g of colorless solid. This material was chromatographed on 50 g of silica gel. Elution with 19:1 hexane:ether gave 0.925 g of colorless solid which recrystallized ethanol. This afforded 0.67 g of colorless plates, m.p. 121°-123°. [α]D25 + 44.69°(c 1.016, CHCl3); uv max (95% EtOH) 278 nm (ε 2020), 287 (1860); ir (CHCl3) 1610, 1580, 1500, 1360 cm-1 ; nmr (CDCl3)δ 7.18 (m, 1), 6.68 (m, 2), 3.74 (s, 3), 3.51 (t, 1, J = Hz), 1.15 ppm (s); ms m/e 356 (M+).

後処理

  1. customwas absorbed (70.5 ml theory)
  2. filtrationThe catalyst was filtered with suction on Celite
  3. washthe filter cake was washed well with ethyl acetate

出典と根拠

ORDレコード
ord-765602a1060f4cda9985c4ddc7d06d76
出典データセット
uspto-grants-1976_01
特許番号
US03933870

反応ノート

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