2,2-Dimethoxypropane → HCID 16122395, 화합물

HRID 1369023

반응식

HRID 1369023 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

HCID 16122395HCID 16122395, 화합물

시약·촉매·용매 1

HCID 8471Triethylamine용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-f22b924b83a54a45bf54fb43ff477152
출처 데이터셋
uspto-grants-2003_06
특허 번호
US06576662B2

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