Pyridine → HCID 67859562, compound

HRID 326189Notes

Reaction equation

HRID 326189 reaction equation
[CH3:1][O:2][C:3](=[O:41])[CH2:4][CH2:5][CH2:6]/[CH:7]=[CH:8]\[CH2:9][C@@H:10]1[C@@H:14](/[CH:15]=[CH:16]/[C@@H:17]([O:26][CH:27]2[CH2:32][CH2:31][CH2:30][CH2:29][O:28]2)[C:18]([CH3:25])([CH3:24])[CH2:19][CH:20]=[C:21]([CH3:23])[CH3:22])[C@H:13]([O:33][CH:34]2[CH2:39][CH2:38][CH2:37][CH2:36][O:35]2)[CH2:12][C@@H:11]1O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Cl)(Cl)(Cl)[Cl:62].N1C=CC=CC=1>CCOCC.CCCCCC.C(#N)C>[CH3:1][O:2][C:3](=[O:41])[CH2:4][CH2:5][CH2:6]/[CH:7]=[CH:8]\[CH2:9][C@@H:10]1[C@@H:14](/[CH:15]=[CH:16]/[C@@H:17]([O:26][CH:27]2[CH2:32][CH2:31][CH2:30][CH2:29][O:28]2)[C:18]([CH3:25])([CH3:24])[CH2:19][CH:20]=[C:21]([CH3:23])[CH3:22])[C@H:13]([O:33][CH:34]2[CH2:39][CH2:38][CH2:37][CH2:36][O:35]2)[CH2:12][C@H:11]1[Cl:62]

Participants

8

Reactant 4

HCID 1049PyridineHCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 67859960HCID 67859960, compound

Product 1

HCID 67859562HCID 67859562, compound

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolventHCID 8058HexaneSolvent

Procedure

A solution of 1.15 g of (5Z,13E)-(8R,9S,11R,12R,15R)-9-hydroxy-11,15-bis(tetrahydropyran-2-yloxy)-16,16,19-trimethyl-5,13,18-prostatrienoic acid methyl ester, 780 mg of triphenylphosphine, and 15 ml of a solution of 0.97 ml of carbon tetrachloride, 0.79 ml of pyridine, and 48 ml of acetonitrile was stirred for 55 hours under argon at room temperature. The mixture was then diluted with 15 ml of ether and 30 ml of hexane, further stirred for 10 minutes, and filtered. The residue from the evaporation was extracted with a mixture of 5 ml of ether and 95 ml of hexane, filtered, and concentrated to dryness under vacuum. The residue was purified by column chromatography on silica gel with hexane/20-50% ethyl acetate as the eluent, thus obtaining 1.07 g of the desired compound.

Workup

  1. filtrationfiltered
  2. customThe residue from the evaporation
  3. extractionwas extracted with a mixture of 5 ml of ether and 95 ml of hexane
  4. filtrationfiltered
  5. concentrationconcentrated to dryness under vacuum
  6. customThe residue was purified by column chromatography on silica gel with hexane/20-50% ethyl acetate as the eluent

Sources & evidence

ORD record
ord-a30cb11cdbb047b5bb30a1e7ab40d891
Source dataset
uspto-grants-1984_04
Patent number
US04444788

Reaction notes

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