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2,2-Dimethoxypropane → HCID 16122395、化合物

HRID 1369023
ノート
印刷プレビュー

反応式

HRID 1369023 の反応式
[CH3:1][C@:2]12[C@H:12]([CH2:13]/[CH:14]=[C:15]3\[C@H:16]([OH:21])[CH2:17][O:18][C:19]\3=[O:20])[C:10](=[CH2:11])[CH2:9][CH2:8][C@@H:7]1[C@@:6]([CH2:23][OH:24])([CH3:22])[C@H:5]([OH:25])[CH2:4][CH2:3]2.CO[C:28](OC)([CH3:30])[CH3:29].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.C1C=CC=CC=1.CS(C)=O>C(N(CC)CC)C>[CH3:1][C@:2]12[C@H:12]([CH2:13]/[CH:14]=[C:15]3\[C@H:16]([OH:21])[CH2:17][O:18][C:19]\3=[O:20])[C:10](=[CH2:11])[CH2:9][CH2:8][C@@H:7]1[C@:6]1([CH3:22])[CH2:23][O:24][C:28]([CH3:30])([CH3:29])[O:25][C@@H:5]1[CH2:4][CH2:3]2
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 4

HCID 64952,2-DimethoxypropaneHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 5318517AndrographolideHCID 18518713Benzene dimethylsulfoxide

生成物 1

HCID 16122395HCID 16122395、化合物

試薬・触媒・溶媒 1

HCID 8471
Triethylamine
溶媒

実験手順

A mixture of andrographolide (15 g), 2,2-dimethoxypropane (20 ml) and catalytic amount of pyridinium p-toluene sulphonate (few crystals) in a solution of benzene/dimethyl suiphoxide (300 ml/40 ml) was refluxed for 30 min. After completion of the reaction (checked by TLC), the contents were cooled to room temperature and basified with excess triethylamine (10 ml) to quench the remaining catalyst. The mixture was diluted with benzene (200 ml) and washed with water (3×300 ml). The organic layer was dried over Na2SO4 and concentrated to obtain a yellow solid which on maceration with diethyl ether gave 3,19-isopropylidene andrographolide as a pale yellow product (15 g). m.p. 194.5° C.

後処理

  1. temperaturewas refluxed for 30 min
  2. customAfter completion of the reaction (checked by TLC)
  3. customto quench the remaining catalyst
  4. additionThe mixture was diluted with benzene (200 ml)
  5. washwashed with water (3×300 ml)
  6. dry with materialThe organic layer was dried over Na2SO4
  7. concentrationconcentrated
  8. customto obtain a yellow solid which on maceration with diethyl ether

出典と根拠

ORDレコード
ord-f22b924b83a54a45bf54fb43ff477152
出典データセット
uspto-grants-2003_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06576662B2

反応ノート

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