Formaldehyde → HCID 13578833, 화합물

HRID 1285310노트

반응식

HRID 1285310 반응식
C[O-].[Na+].[CH3:4][C@:5]12[CH2:22][CH:21]=[C:20]3[C@@H:10]([CH2:11][CH2:12][C:13]4[C@:18]3([CH3:19])[CH:17]=[CH:16][C:15](=[O:23])[CH:14]=4)[C@@H:9]1[CH2:8][CH2:7][C:6]2=[O:24].[CH3:25]OC(=O)C(OC)=O.C=O>CO.C1COCC1.C(Cl)Cl.O.C(N(CC)CC)C.C(O)(=O)C>[CH2:25]=[C:7]1[CH2:8][C@H:9]2[C@H:10]3[C:20](=[CH:21][CH2:22][C@:5]2([CH3:4])[C:6]1=[O:24])[C@:18]1([CH3:19])[C:13](=[CH:14][C:15](=[O:23])[CH:16]=[CH:17]1)[CH2:12][CH2:11]3

참가 물질

11

반응물 4

HCID 712FormaldehydeHCID 11120Dimethyl oxalateHCID 10265807Androsta-1,4,9(11)-triene-3,17-dioneHCID 10942334Sodium Methoxide

생성물 1

HCID 13578833HCID 13578833, 화합물

시약·촉매·용매 6

HCID 176Acetic Acid용매HCID 887Methanol용매2회HCID 962Water용매HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매HCID 8471Triethylamine용매

실험 절차

Sodium methoxide in methanol (25%, 6.85 ml) is added dropwise to a mixture of androst-1,4,9(11)-triene-3,17-dione (IB, 7.05 g) in THF (80 ml) and methylene chloride (8 ml) containing dimethyloxalate (4.38 g) previously cooled to 4°. After one hour at 4°, the preparation of the 16-oxalate salt is complete and the following reagents were added sequentially: acetic acid (0.5 ml), triethylamine (2.6 ml), methanol (10 ml), and aqueous formaline (37%, 2.8 ml). The reaction mixture was warmed to 20°-25° and after one hour the reaction was complete. The reaction mixture was poured into water and extracted twice with ethyl acetate. The ethyl acetate extracts were combined, washed with water, dried over sodium sulfate, and concentrated under reduced pressure to a solid. The solid was dissolved in methylene chloride (2.5 ml), following which the methylene chloride was evaporated. The solid was again dissolved in dry THF (25 ml), following which the THF was evaporated. The solid was then dissolved in dry THF (50 ml) for use in the following reaction.

후처리

  1. temperaturepreviously cooled to 4°
  2. additionthe following reagents were added sequentially
  3. temperatureThe reaction mixture was warmed to 20°-25° and after one hour the reaction
  4. extractionextracted twice with ethyl acetate
  5. washwashed with water
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under reduced pressure to a solid
  8. dissolutionThe solid was dissolved in methylene chloride (2.5 ml)
  9. customwas evaporated
  10. dissolutionThe solid was again dissolved in dry THF (25 ml)
  11. customwas evaporated
  12. dissolutionThe solid was then dissolved in dry THF (50 ml) for use in the following reaction

출처 및 근거

ORD 기록
ord-45c51960a26d4961abdf2d8e6e0fa701
출처 데이터셋
uspto-grants-1986_01
특허 번호
US04567001

반응 노트

불러오는 중…