Acetic Acid → HCID 13578833, 화합물

HRID 1285309노트

반응식

HRID 1285309 반응식
[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

참가 물질

9

반응물 4

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

생성물 1

HCID 13578833HCID 13578833, 화합물

시약·촉매·용매 4

HCID 887Methanol용매2회HCID 962Water용매HCID 8028Tetrahydrofuran용매HCID 8471Triethylamine용매

실험 절차

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°.

후처리

  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

출처 및 근거

ORD 기록
ord-86b9f26997c14649b08e42908ccdaeab
출처 데이터셋
uspto-grants-1986_01
특허 번호
US04567001

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