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4-Toluenesulfonyl chloride → HCID 86738249, compound

HRID 1447052
Notes
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Reaction equation

HRID 1447052 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[CH3:12][O:13][C:14](=[O:49])[CH2:15][CH2:16][CH2:17]/[CH:18]=[CH:19]\[CH2:20][C@@H:21]1[C@@H:25](/[CH:26]=[CH:27]/[C@@H:28]([O:34][CH:35]2[CH2:40][CH2:39][CH2:38][CH2:37][O:36]2)[CH2:29][CH2:30][C:31]#[C:32][CH3:33])[C@H:24]([O:41][CH:42]2[CH2:47][CH2:46][CH2:45][CH2:44][O:43]2)[CH2:23][C@@H:22]1[OH:48].[N+](=C)=[N-].C(=O)(O)[O-].[Na+]>CCOCC.O.N1C=CC=CC=1>[CH3:12][O:13][C:14](=[O:49])[CH2:15][CH2:16][CH2:17]/[CH:18]=[CH:19]\[CH2:20][C@@H:21]1[C@@H:25](/[CH:26]=[CH:27]/[C@@H:28]([O:34][CH:35]2[CH2:40][CH2:39][CH2:38][CH2:37][O:36]2)[CH2:29][CH2:30][C:31]#[C:32][CH3:33])[C@H:24]([O:41][CH:42]2[CH2:47][CH2:46][CH2:45][CH2:44][O:43]2)[CH2:23][C@@H:22]1[O:48][S:7]([C:4]1[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=1)(=[O:9])=[O:8]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 9550DiazomethaneHCID 516892Sodium BicarbonateHCID 70548451HCID 70548451, compound

Product 1

HCID 86738249HCID 86738249, compound

Reagents, catalysts & solvents 3

HCID 962
Water
Solvent
3×
HCID 1049PyridineSolvent
HCID 3283Diethyl EtherSolvent

Procedure

At 0°, 1.38 g. of p-toluenesulfonyl chloride is added to a solution of 2 g. of (5Z,13E)-(9S,11R,15S)-11,15-bis(tetrahydropyran-2-yloxy)-9-hydroxy-5,13-prostadien-18-ynoic methyl ester (prepared from the corresponding acid with ethereal diazomethane solution) in 4 ml. of pyridine. The mixture is stirred for 6 hours at room temperature and then allowed to stand at 5° for 60 hours. The mixture is then diluted with ether, shaken in succession once with water, once with ice-cold 3% sulfuric acid, once with water, once with 5% sodium bicarbonate solution, twice with water, and dried over magnesium sulfate and evaporated under vacuum, thus obtaining 2.45 g. of the title compound as a colorless oil.

Workup

  1. customAt 0°
  2. waitto stand at 5° for 60 hours
  3. dry with materialdried over magnesium sulfate
  4. customevaporated under vacuum
  5. customthus obtaining 2.45 g

Sources & evidence

ORD record
ord-c0dbaa7c95ec4633931e79d9b077f0eb
Source dataset
uspto-grants-1982_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04315013

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes