Pyridine → HCID 86739382, compound

HRID 1590922Notes

Reaction equation

HRID 1590922 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](\[Cl: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]1O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:60]([Cl:64])(Cl)(Cl)Cl.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](\[Cl: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:60]1[Cl:64]

Participants

8

Reactant 4

HCID 1049PyridineHCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 86739383HCID 86739383, compound

Product 1

HCID 86739382HCID 86739382, compound

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolventHCID 8058HexaneSolvent

Procedure

A solution of 1.16 g of (5Z,13E,18Z)-(8R,9S,11R,12R,15S,16RS)-9-hydroxy-19-chloro-16-methyl-11,15-bis(tetrahydropyran-2-yloxy)-5,13,18-prostatrienoic acid methyl ester, 785 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 under argon at room temperature for 65 hours. The mixture was then diluted with 15 ml of ether and 30 ml of hexane, further stirred for 10 minutes, and filtered. The evaporation residue 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/10-50% ethyl acetate as the eluent. In this way, 457 mg of the desired compound was isolated.

Workup

  1. filtrationfiltered
  2. extractionThe evaporation residue was extracted with a mixture of 5 ml of ether and 95 ml of hexane
  3. filtrationfiltered
  4. concentrationconcentrated to dryness under vacuum
  5. customThe residue was purified by column chromatography on silica gel with hexane/10-50% ethyl acetate as the eluent

Sources & evidence

ORD record
ord-3812fc6e9e844c69bf0355bef3cf2014
Source dataset
uspto-grants-1993_04
Patent number
US05204371

Reaction notes

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