Pyridine → HCID 15307271、化合物

HRID 850831ノート

反応式

HRID 850831 の反応式
[OH:1][C:2]1[CH:19]=[CH:18][C:17]2[C@@H:16]3[C:7]([C@H:8]4[C@@:12]([CH2:14][CH2:15]3)([CH3:13])[C:11](=[O:20])[CH2:10][CH2:9]4)=[CH:6][CH2:5][C:4]=2[CH:3]=1.C1(C)C=CC(S(O)(=O)=[O:28])=CC=1.N1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>O1CCCC1.O1C=CCCC1.C(OCC)(=O)C>[O:28]1[CH2:37][CH2:36][CH2:35][CH2:34][CH:33]1[O:1][C:2]1[CH:19]=[CH:18][C:17]2[C@@H:16]3[C:7]([C@H:8]4[C@@:12]([CH2:14][CH2:15]3)([CH3:13])[C:11](=[O:20])[CH2:10][CH2:9]4)=[CH:6][CH2:5][C:4]=2[CH:3]=1

参加物

7

反応物 3

HCID 1049PyridineHCID 6101p-Toluenesulfonic acidHCID 223368Equilin

生成物 1

HCID 15307271HCID 15307271、化合物

試薬・触媒・溶媒 3

HCID 8028Tetrahydrofuran溶媒HCID 80803,4-dihydro-2H-pyran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A suspension of 2.0 g of 3-hydroxy-estra-1,3,5(10),7-tetraen-17-one in 20 ml of tetrahydrofuran and 2.0 ml of dihydropyran is stirred with 9.6 mg of para-toluenesulfonic acid for 24 hours at room temperature. Then, 0.3 ml of pyridine is added, diluted with ethyl acetate, washed with sodium bicarbonate solution as well as with saturated sodium chloride solution, dried on sodium sulfate, concentrated by evaporation in a vacuum, and chromatographed on silica gel with hexane/acetone. 1.9 g of 3-tetrahydropyranyloxy-estra-1,3,5(10),7-tetraen-17-one is obtained as colorless crystals with a melting point of 147-149° C., [α]D22 =+209.7° (c=0.5% in pyridine).

後処理

  1. washwashed with sodium bicarbonate solution as well as with saturated sodium chloride solution
  2. customdried on sodium sulfate
  3. concentrationconcentrated by evaporation in a vacuum
  4. customchromatographed on silica gel with hexane/acetone

出典と根拠

ORDレコード
ord-e4de52cbfd0e4196984a581ca8dad1eb
出典データセット
uspto-grants-2000_01
特許番号
US06018062

反応ノート

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