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2,2-Dimethoxypropane → HCID 16122395, compound

HRID 1019229
Notes
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Reaction equation

HRID 1019229 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.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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 64952,2-DimethoxypropaneHCID 8471TriethylamineHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 5318517Andrographolide

Product 1

HCID 16122395HCID 16122395, compound

Reagents, catalysts & solvents 1

HCID 18518713
Benzene dimethylsulfoxide
Solvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-8d0099e683f24283b1e586a65c8c8765
Source dataset
uspto-grants-2002_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06486196B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes