Pyridine → HCID 67859862, compound

HRID 326191Notes

Reaction equation

HRID 326191 reaction equation
[CH3:1][O:2][C:3](=[O:39])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C@@H:10]1[C@@H:14](/[CH:15]=[CH:16]/[C@@H:17]([O:24][CH:25]2[CH2:30][CH2:29][CH2:28][CH2:27][O:26]2)[CH2:18][CH2:19][CH:20]=[C:21]([CH3:23])[CH3:22])[C@H:13]([O:31][CH:32]2[CH2:37][CH2:36][CH2:35][CH2:34][O:33]2)[CH2:12][C@@H:11]1O.C(Cl)(Cl)(Cl)[Cl:41].N1C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CCOCC.CCCCCC.C(#N)C>[CH3:1][O:2][C:3](=[O:39])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C@@H:10]1[C@@H:14](/[CH:15]=[CH:16]/[C@@H:17]([O:24][CH:25]2[CH2:30][CH2:29][CH2:28][CH2:27][O:26]2)[CH2:18][CH2:19][CH:20]=[C:21]([CH3:23])[CH3:22])[C@H:13]([O:31][CH:32]2[CH2:37][CH2:36][CH2:35][CH2:34][O:33]2)[CH2:12][C@H:11]1[Cl:41]

Participants

8

Reactant 4

HCID 1049PyridineHCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 67859806HCID 67859806, compound

Product 1

HCID 67859862HCID 67859862, compound

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolventHCID 8058HexaneSolvent

Procedure

A solution of 1.0 g of (13E)-(8R,9S,11R,12R,15S)-9-hydroxy-19-methyl-11,15-bis(tetrahydropyran-2-yloxy)-13,18-prostadienoic acid methyl ester in 14 ml of a solution of 0.97 ml of carbon tetrachloride, 0.79 ml of pyridine, and 48 ml of acetonitrile was stirred together with 730 mg of triphenylphosphine for 70 hours at room temperature under argon. Thereafter the mixture was diluted with 16 ml of ether and 32 ml of hexane, further agitated for 10 minutes, filtered, and concentrated by means of a forced circulation evaporator. 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 chromatograpy on silica gel with hexane/20% ethyl acetate as the eluent, thus obtaining 720 mg of the title compound.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated by means of a forced circulation evaporator
  3. extractionThe evaporation residue was 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 chromatograpy on silica gel with hexane/20% ethyl acetate as the eluent

Sources & evidence

ORD record
ord-b7ae9aef65a74d818e348c176e59c35b
Source dataset
uspto-grants-1984_04
Patent number
US04444788

Reaction notes

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