p-Toluenesulfonic acid → HCID 57857057, compound

HRID 561745Notes

Reaction equation

HRID 561745 reaction equation
[S:1]1[C:5]([C@H:6]([O:26][Si:27]([C:40]([CH3:43])([CH3:42])[CH3:41])([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)/[CH:7]=[CH:8]/[C@H:9]2[C:13](=[O:14])[CH2:12][C@H:11]([OH:15])[C@@H:10]2[CH2:16]/[CH:17]=[CH:18]\[CH2:19][CH2:20][CH2:21][C:22]([O:24][CH3:25])=[O:23])=[CH:4][C:3]2[CH:44]=[CH:45][CH:46]=[CH:47][C:2]1=2.[O:48]1[CH:53]=[CH:52][CH2:51][CH2:50][CH2:49]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(Cl)Cl.[Cl-].[Na+].O>[S:1]1[C:5]([C@H:6]([O:26][Si:27]([C:40]([CH3:43])([CH3:42])[CH3:41])([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)/[CH:7]=[CH:8]/[C@H:9]2[C:13](=[O:14])[CH2:12][C@H:11]([O:15][CH:49]3[CH2:50][CH2:51][CH2:52][CH2:53][O:48]3)[C@@H:10]2[CH2:16]/[CH:17]=[CH:18]\[CH2:19][CH2:20][CH2:21][C:22]([O:24][CH3:25])=[O:23])=[CH:4][C:3]2[CH:44]=[CH:45][CH:46]=[CH:47][C:2]1=2

Participants

6

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 80803,4-dihydro-2H-pyranHCID 57857008HCID 57857008, compound

Product 1

HCID 57857057HCID 57857057, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

(Z)-Methyl 7-((1R,2R,5S)-2-((R,E)-3-(benzo[b]thiophen-2-yl)-3-(tert-butyldiphenylsilyloxy)prop-1-enyl)-5-hydroxy-3-oxocyclopentyl)hept-5-enoate (11a, limiting reagent) is dissolved in DCM (0.1 M) under a nitrogen atmosphere. Dihydropyran (1.1 molar equivalent) is added, followed by a catalytic amount of p-toluenesulfonic acid. The reaction is stirred at room temperature under a nitrogen atmosphere and the reaction progress is monitored by TLC. Upon completion, brine is added to the reaction mixture and the layers are separated. The organic phase is dried over sodium sulfate, filtered, and the solvent is evaporated. The crude product is purified by flash chromatography on regular silica gel eluted with hexanes-ethyl acetate to afford the title intermediate 15a.

Workup

  1. customthe layers are separated
  2. dry with materialThe organic phase is dried over sodium sulfate
  3. filtrationfiltered
  4. customthe solvent is evaporated
  5. customThe crude product is purified by flash chromatography on regular silica gel
  6. washeluted with hexanes-ethyl acetate

Sources & evidence

ORD record
ord-599eb3930268401ea6f915b421010a20
Source dataset
uspto-grants-2011_11
Patent number
US08063240B2

Reaction notes

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