Acetone → HCID 66931861, 화합물

HRID 2382224노트

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HRID 2382224 반응식
[BH4-].[Na+].[CH2:3]1[CH2:25][O:24][C:5]2([CH2:22][CH2:21][C:20]3[C:19]4[C@H:10]([C@H:11]5[C@@:15]([CH2:17][CH:18]=4)([CH3:16])[C:14](=[O:23])[CH2:13][CH2:12]5)[CH2:9][CH2:8][C:7]=3[CH2:6]2)[O:4]1.CC(C)=O.[Cl-].[Na+]>[OH-].[Na+].CO.C(OCC)(=O)C.O>[CH2:25]1[CH2:3][O:4][C:5]2([CH2:22][CH2:21][C:20]3[C:19]4[C@H:10]([C@H:11]5[C@@:15]([CH2:17][CH:18]=4)([CH3:16])[CH:14]([OH:23])[CH2:13][CH2:12]5)[CH2:9][CH2:8][C:7]=3[CH2:6]2)[O:24]1

참가 물질

9

반응물 4

HCID 180AcetoneHCID 5234Sodium ChlorideHCID 4311764Sodium borohydrideHCID 7076399Estra-5(10),9(11)-diene-3,17-dione, cyclic 3-(1,2-ethanediyl acetal)

생성물 1

HCID 66931861HCID 66931861, 화합물

시약·촉매·용매 4

HCID 887Methanol용매HCID 962Water용매HCID 8857Ethyl Acetate용매HCID 14798Sodium Hydroxide용매

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온도
2 °C

실험 절차

Sodium borohydride (MW=37.8; 18.9 g; 500 mmol) dissolved in 0.5 N sodium hydroxide (100 ml) was introduced over about 5 min at around 2° C. into a suspension of 3,3-ethylenedioxyestra-5(10),9(11)-diene-17-one (MW=314.4; 100 g; 318 mmol) in methanol (1 liter). The medium was stirred for 2 h at around 2° C. and then acetone (100 ml) was introduced over about 15 min at around 5° C. The medium was stirred for 1 h, and poured at around 20° C. into the stirred mixture of water (2 liters), sodium chloride (500 g) and ethyl acetate (400 ml). The medium was separated by decantation and the aqueous phase was re-extracted with ethyl acetate. The combined organic phases were washed with water, dried over sodium sulfate and concentrated at atmospheric pressure at 500 ml. The distillation is continued while the volume is kept constant by gradual introduction of 1,2-dimethoxyethane (DME). The temperature at the end of the exchange is 83° C. The solution was used as it is in the next step, but a dry extract gave the expected product (resin). C20H28O3; MW=316.4.

후처리

  1. stirringThe medium was stirred for 1 h
  2. customThe medium was separated by decantation
  3. extractionthe aqueous phase was re-extracted with ethyl acetate
  4. washThe combined organic phases were washed with water
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated at atmospheric pressure at 500 ml
  7. distillationThe distillation
  8. customis 83° C
  9. extractiona dry extract

출처 및 근거

ORD 기록
ord-b2f3223b90bb45329aef40a43c494928
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08258328B2

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