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Neopentyl glycol → 20-(5,5-Dimethyl-1,3-dioxan-2-yl)-7alpha-hydroxypregna-1,4-dien-3one

HRID 1708742
ノート
印刷プレビュー

反応式

HRID 1708742 の反応式
[OH:1][C@@H:2]1[CH2:22][C:21]2[C@:16]([CH3:24])([CH:17]=[CH:18][C:19](=[O:23])[CH:20]=2)[C@@H:15]2[C@@H:3]1[C@H:4]1[C@:12]([CH3:25])([CH2:13][CH2:14]2)[C@@H:7]([CH:8]([CH:10]=[O:11])[CH3:9])[CH2:6][CH2:5]1.[CH3:26][C:27]([CH3:32])([CH2:30]O)[CH2:28][OH:29].C(OCC)(=O)C.CCCCCC>C(Cl)Cl.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH3:26][C:27]1([CH3:32])[CH2:28][O:29][CH:10]([CH:8]([C@@H:7]2[C@:12]3([CH3:25])[C@H:4]([C@H:3]4[C@H:15]([CH2:14][CH2:13]3)[C@:16]3([CH3:24])[C:21](=[CH:20][C:19](=[O:23])[CH:18]=[CH:17]3)[CH2:22][C@H:2]4[OH:1])[CH2:5][CH2:6]2)[CH3:9])[O:11][CH2:30]1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 31344Neopentyl glycolHCID 21226206Ethyl acetate hexaneHCID 228438847-Hydroxy-pregna-1,4-dien-3-one-20-carbaldehyde

生成物 1

HCID 2284393020-(5,5-Dimethyl-1,3-dioxan-2-yl)-7alpha-hydroxypregna-1,4-dien-3one収率 50.2%

試薬・触媒・溶媒 2

HCID 6101p-Toluenesulfonic acid触媒
HCID 6344
Dichloromethane
溶媒

実験手順

In 200 ml of methylene chloride were dissolved 5.00 g (14.6 mmoles) of 7α-hydroxypregna-1,4-dien-3-one-20-carbaldehyde and 4.56 g (43.8 mmoles) of 2,2-dimethyl-1,3-propanediol, followed by addition of 100 mg of p-toluenesulfonic acid and 20 g of molecular sieve 4A 1/16. The mixture was stirred-gently at room temperature for 12 hours. From the reaction mixture thus obtained, the molecular sieve was filtered off and the solvent in the filtrate was distilled off under reduced pressure. Finally the residue was purified by silica gel chromatography (eluent:ethyl acetate-hexane=1:10, v/v) to give 3.14 g of 20-(5,5-dimethyl-1,3-dioxan-2-yl)-7α-hydroxypregna-1,4-dien-3-one (yield: 50%).

後処理

  1. customFrom the reaction mixture thus obtained
  2. filtrationthe molecular sieve was filtered off
  3. distillationthe solvent in the filtrate was distilled off under reduced pressure
  4. customFinally the residue was purified by silica gel chromatography (eluent

出典と根拠

ORDレコード
ord-3272134c072749e6b553ca8451ac9789
出典データセット
uspto-grants-1994_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05359055

反応ノート

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