2,2-Dimethoxypropane → HCID 16122395, 화합물

HRID 1019229

반응식

HRID 1019229 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.C(N(CC)CC)C>C1C=CC=CC=1.CS(C)=O>[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 8471TriethylamineHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 5318517Andrographolide

생성물 1

HCID 16122395HCID 16122395, 화합물

시약·촉매·용매 1

HCID 18518713Benzene dimethylsulfoxide용매

실험 절차

A mixture of andrographolide (15 g), 2,2-dimethoxy propane (20 ml) and a catalytic amount of pyridinium p-toluene sulphonate in benzene/dimethyl sulphoxide (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 treated with excess triethylamine (10 ml) to quench the remaining catalyst. The reaction mixture was diluted with benzene (200 ml) and washed with water (3×300 ml). The organic layer was separated, dried over Na2SO4 and concentrated to obtain a yellow coloured solid which on maceration with diethyl ether gave 3,19-isopropylidene andrographolide as a pale yellow product (16.5 g). m.p. 194.5° C., m/z 390.

후처리

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

출처 및 근거

ORD 기록
ord-8d0099e683f24283b1e586a65c8c8765
출처 데이터셋
uspto-grants-2002_11
특허 번호
US06486196B2

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