Acetic Acid → HCID 86741443、化合物

HRID 543023ノート

反応式

HRID 543023 の反応式
[CH2:1]([Li])[CH2:2][CH2:3][CH3:4].[O:6]=[C:7]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])CP(=O)([O-])[O-].[C:24]([O:27][C@H:28]1[CH2:33][CH2:32][C@H:31]2[C@H:34]3[C@H:43]([CH2:44][CH2:45][C@:29]12[CH3:30])[C:42]1[CH:41]=[CH:40][C:39]([O:46][C:47](=[O:54])[C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)=[CH:38][C:37]=1[CH2:36][C@H:35]3CCC=O)(=[O:26])[CH3:25].C(O)(=O)C>CCCCCC.O1CCCC1>[C:24]([O:27][C@H:28]1[CH2:33][CH2:32][C@H:31]2[C@H:34]3[C@H:43]([CH2:44][CH2:45][C@:29]12[CH3:30])[C:42]1[CH:41]=[CH:40][C:39]([O:46][C:47](=[O:54])[C:48]2[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=2)=[CH:38][C:37]=1[CH2:36][C@H:35]3[CH2:4][CH2:3][CH:2]=[CH:1][C:7](=[O:6])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])(=[O:26])[CH3:25]

参加物

7

反応物 4

HCID 176Acetic AcidHCID 20206901HCID 20206901、化合物HCID 86741444HCID 86741444、化合物HCID 178418339Butyllithium

生成物 1

HCID 86741443HCID 86741443、化合物

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8058Hexane溶媒

反応条件

温度
-70 °C

実験手順

n-Butyl-lithium (0.341 ml. of a 1.6 molar solution in hexane) was added to a stirred solution of 2-oxotridecylphosphonate (0.193 g.) in tetrahydrofuran (10 ml.) which was maintained at -70° C. and the mixture was stirred at that temperature for 40 minutes. A solution of 3-(17β-acetoxy-3-benzoyloxyoestra-1,3,5(10)-trien-7α-yl)propionaldehyde (Example 3; 0.2 g.) in tetrahydrofuran (10 ml.) was added and the mixture was allowed to warm up to laboratory temperature and was stirred at that temperature for 4.5 hours. Acetic acid was added until the mixture was acidic and the mixture was evaporated to dryness. Water (10 ml.) was added and the mixture was extracted three times with ethyl acetate (30 ml. each time). The combined extracts were washed with water, dried and evaporated to dryness and there was thus obtained as residual oil 1-(17β-acetoxy-3-benzoyloxyoestra-1,3,5(10)-trien-7α-yl)hexadec-3-en-5-one.

後処理

  1. temperatureto warm up to laboratory temperature
  2. stirringwas stirred at that temperature for 4.5 hours
  3. customthe mixture was evaporated to dryness
  4. additionWater (10 ml.) was added
  5. extractionthe mixture was extracted three times with ethyl acetate (30 ml
  6. washThe combined extracts were washed with water
  7. customdried
  8. customevaporated to dryness and there

出典と根拠

ORDレコード
ord-580000efe708484dae508ec6c63cbafd
出典データセット
uspto-grants-1987_04
特許番号
US04659516

反応ノート

読み込み中…