Pyridine → HCID 67859585, compound

HRID 326182Notes

Reaction equation

HRID 326182 reaction equation
[CH3:1][O:2][C:3](=[O:40])[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:25][CH:26]2[CH2:31][CH2:30][CH2:29][CH2:28][O:27]2)[CH:18]([CH3:24])[CH2:19][CH:20]=[C:21]([CH3:23])[CH3:22])[C@H:13]([O:32][CH:33]2[CH2:38][CH2:37][CH2:36][CH2:35][O:34]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:61].N1C=CC=CC=1>CCOCC.CCCCCC.C(#N)C>[CH3:1][O:2][C:3](=[O:40])[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:25][CH:26]2[CH2:31][CH2:30][CH2:29][CH2:28][O:27]2)[CH:18]([CH3:24])[CH2:19][CH:20]=[C:21]([CH3:23])[CH3:22])[C@H:13]([O:32][CH:33]2[CH2:38][CH2:37][CH2:36][CH2:35][O:34]2)[CH2:12][C@H:11]1[Cl:61]

Participants

8

Reactant 4

HCID 1049PyridineHCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 13097069HCID 13097069, compound

Product 1

HCID 67859585HCID 67859585, compound

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolventHCID 8058HexaneSolvent

Procedure

A solution of 1.09 g of (5Z,13E)-(8R,9S,11R,12R,15S,16RS)-9-hydroxy-11,15-bis(tetrahydropyran-2-yloxy)-16,19-dimethyl-5,13,18-prostatrienoic acid methyl ester, 760 mg of triphenylphosphine, and 14.5 ml of a solution of 0.97 ml of carbon tetrachloride, 0.79 ml of pyridine, and 48 ml of acetonitrile were agitated under argon at room temperature for 69 hours. 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 evaporated to dryness under vacuum. The residue was purified by column chromatography on silica gel with hexane/20-33% ethyl acetate as the eluent, thus isolating 1.04 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. customevaporated to dryness under vacuum
  6. customThe residue was purified by column chromatography on silica gel with hexane/20-33% ethyl acetate as the eluent

Sources & evidence

ORD record
ord-61bfb1d6437248639ac06f2272c06a47
Source dataset
uspto-grants-1984_04
Patent number
US04444788

Reaction notes

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