Formaldehyde → 3Betahydroxymethoxy-5-androsten-17-one acetate

HRID 1984

반응식

HRID 1984 반응식
[CH3:1][C@@:2]12[C:10](=[O:11])[CH2:9][CH2:8][C@H:7]1[C@@H:6]1[CH2:12][CH:13]=[C:14]3[CH2:19][C@@H:18]([OH:20])[CH2:17][CH2:16][C@:15]3([CH3:21])[C@H:5]1[CH2:4][CH2:3]2.[H-].[Na+].[C:24]([O:27]CCl)(=[O:26])[CH3:25].[C:30](Cl)(=[O:32])C.C=O>C1COCC1.[Cl-].[Cl-].[Zn+2].O>[C:24]([OH:27])(=[O:26])[CH3:25].[OH:32][CH2:30][O:20][C@H:18]1[CH2:17][CH2:16][C@@:15]2([CH3:21])[C:14](=[CH:13][CH2:12][C@@H:6]3[C@@H:5]2[CH2:4][CH2:3][C@@:2]2([CH3:1])[C@H:7]3[CH2:8][CH2:9][C:10]2=[O:11])[CH2:19]1

참가 물질

9

반응물 5

HCID 712FormaldehydeHCID 5881DehydroepiandrosteroneHCID 6367Acetyl chlorideHCID 24758Sodium hydride2회HCID 69366Chloromethyl acetate

생성물 1

HCID 1317205663Betahydroxymethoxy-5-androsten-17-one acetate

시약·촉매·용매 3

HCID 3007855Zincchloride촉매HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of dehydroepiandrosterone (2.88 g, 10 mmol) in THF (100 mL) is added sodium hydride (11 mmol, 60% in oil) at room temperature under an argon atmosphere. When all the sodium hydride has reacted, chloromethyl acetate (prepared from acetyl chloride and formaldehyde (or derivative) using ZnCl2 as catalyst) is added and the mixture is heated for a few hours. After cooling, the mixture is poured into water and extracted with ethyl acetate. The organic phase is then washed with water, dried, filtered and evaporated to dryness to give the desired compound.

후처리

  1. additionis added
  2. temperaturethe mixture is heated for a few hours
  3. temperatureAfter cooling
  4. extractionextracted with ethyl acetate
  5. washThe organic phase is then washed with water
  6. customdried
  7. filtrationfiltered
  8. customevaporated to dryness

출처 및 근거

ORD 기록
ord-6642d755fcb048beb2e3a7e3e3b838c6
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05728688

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