2,2-Dimethoxypropane → HCID 16122395, compound

HRID 1369023

Reaction equation

HRID 1369023 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

HCID 16122395HCID 16122395, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-f22b924b83a54a45bf54fb43ff477152
Source dataset
uspto-grants-2003_06
Patent number
US06576662B2

Linked notes

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