Acetic Acid → HCID 13578833、化合物

HRID 1285309ノート

反応式

HRID 1285309 の反応式
[CH3:1][C@:2]12[CH2:19][CH:18]=[C:17]3[C@@H:7]([CH2:8][CH2:9][C:10]4[C@:15]3([CH3:16])[CH:14]=[CH:13][C:12](=[O:20])[CH:11]=4)[C@@H:6]1[CH2:5][CH2:4][C:3]2=[O:21].C[O-].[Na+].[C:25](O)(=O)C.C=O>C1COCC1.CO.O.C(N(CC)CC)C>[CH2:25]=[C:4]1[CH2:5][C@H:6]2[C@H:7]3[C:17](=[CH:18][CH2:19][C@:2]2([CH3:1])[C:3]1=[O:21])[C@:15]1([CH3:16])[C:10](=[CH:11][C:12](=[O:20])[CH:13]=[CH:14]1)[CH2:9][CH2:8]3

参加物

9

反応物 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 10265807Androsta-1,4,9(11)-triene-3,17-dioneHCID 10942334Sodium Methoxide

生成物 1

HCID 13578833HCID 13578833、化合物

試薬・触媒・溶媒 4

HCID 887Methanol溶媒2 回HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒HCID 8471Triethylamine溶媒

実験手順

Androsta-1,4,9(11)-triene-3,17-dione (IB, 0.7 g) in THF (8 ml) and dimethyloxylate (0.44 g) were combined and cooled to 3° in an ice bath. Sodium methoxide in methanol (25%, 0.685 ml) was added dropwise with no temperature rise. TLC after about 1/2 hr showed the reaction was nearly completed. Acetic acid (0.05 ml), triethylamine (0.26 ml) and methanol (1 ml) were added. Formaldehyde (37%, 0.28 ml) was added and the reaction mixture stirred at 20°-25°. TLC, after approximately 11/2 hrs. showed the reaction was complete. The reaction mixture was added to water and extracted with ethyl acetate. The layers were separated, the aqueous layer was extracted with ethyl acetate and combined with the organic extract. The combined organic extract was washed with water and separated from the organic layer. Methylene chloride was added and the mixture dried over sodium sulfate. The mixture was filtered and the filtrate was concentrated under reduced pressure to an oil. Acetone was added and the title compound was obtained upon crystallization, m.p. 157°-160°.

後処理

  1. temperaturecooled to 3° in an ice bath
  2. custom2 hrs
  3. extractionextracted with ethyl acetate
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted with ethyl acetate
  6. extractionThe combined organic extract
  7. washwas washed with water
  8. customseparated from the organic layer
  9. additionMethylene chloride was added
  10. dry with materialthe mixture dried over sodium sulfate
  11. filtrationThe mixture was filtered
  12. concentrationthe filtrate was concentrated under reduced pressure to an oil
  13. additionAcetone was added

出典と根拠

ORDレコード
ord-86b9f26997c14649b08e42908ccdaeab
出典データセット
uspto-grants-1986_01
特許番号
US04567001

反応ノート

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