HCID 86613972, compound → HCID 86613973, compound

HRID 1920710Notes

Reaction equation

HRID 1920710 reaction equation
C([O:4][C@H:5]1[C@H:10]([O:11][C:12](=[O:19])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C@@H:9]([CH2:20][O:21][C:22](=[O:29])[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[O:8][C@H:7]([O:30][C@H:31]2[C@H:36]([O:37][C:38](=[O:45])[C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[C@@H:35]([CH2:46][O:47][C:48](=[O:55])[C:49]3[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=3)[O:34][C@H:33]([O:56][C@H:57]3[C@@H:70]([O:71][CH2:72][C:73]4[CH:78]=[CH:77][CH:76]=[CH:75][CH:74]=4)[C@H:69]([O:79][CH2:80][C:81]4[CH:86]=[CH:85][CH:84]=[CH:83][CH:82]=4)[C@@H:68]([CH2:87][O:88][CH2:89][C:90]4[CH:95]=[CH:94][CH:93]=[CH:92][CH:91]=4)[O:67][C@@H:58]3[O:59][CH2:60][C:61]3[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=3)[C@H:32]2[O:96][C:97](=[O:104])[C:98]2[CH:103]=[CH:102][CH:101]=[CH:100][CH:99]=2)[C@H:6]1[O:105][C:106](=[O:113])[C:107]1[CH:112]=[CH:111][CH:110]=[CH:109][CH:108]=1)C=C>CO.ClCCCl.Cl[Pd]Cl>[C:106]([O:105][C@H:6]1[C@@H:5]([OH:4])[C@H:10]([O:11][C:12](=[O:19])[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[C@@H:9]([CH2:20][O:21][C:22](=[O:29])[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[O:8][C@@H:7]1[O:30][C@H:31]1[C@H:36]([O:37][C:38](=[O:45])[C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=2)[C@@H:35]([CH2:46][O:47][C:48](=[O:55])[C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)[O:34][C@H:33]([O:56][C@H:57]2[C@@H:70]([O:71][CH2:72][C:73]3[CH:74]=[CH:75][CH:76]=[CH:77][CH:78]=3)[C@H:69]([O:79][CH2:80][C:81]3[CH:82]=[CH:83][CH:84]=[CH:85][CH:86]=3)[C@@H:68]([CH2:87][O:88][CH2:89][C:90]3[CH:95]=[CH:94][CH:93]=[CH:92][CH:91]=3)[O:67][C@@H:58]2[O:59][CH2:60][C:61]2[CH:62]=[CH:63][CH:64]=[CH:65][CH:66]=2)[C@H:32]1[O:96][C:97](=[O:104])[C:98]1[CH:103]=[CH:102][CH:101]=[CH:100][CH:99]=1)(=[O:113])[C:107]1[CH:108]=[CH:109][CH:110]=[CH:111][CH:112]=1

Participants

5

Reactant 1

HCID 86613972HCID 86613972, compound

Product 1

HCID 86613973HCID 86613973, compoundYield 88.3%

Reagents, catalysts & solvents 3

HCID 24290Palladium ChlorideCatalystHCID 111,2-DichloroethaneSolventHCID 887MethanolSolvent

Procedure

PdCl2 (40 mg) was added to a solution of the allyl ether (26) (394 mg, 241 μmol) in MeOH (10 mL) and 1,2-DCE (10 mL) and the combined mixture was heated (70°, 60 min). After the time, the solvents were evaporated and the residue subjected to FC (20-30% EtOAc/hexanes) to yield the alcohol (27) as a colourless oil (317 mg, 84%). 1H NMR (CDCl3) δ 3.67-3.82, 3.91-3.99, 4.01-4.21, 4.29-4.71 (4 m, 21 H; H-2I,-3I,-4I,-5I,-6aI,-6bI,-3II,-5II,-6aI,-6bII,-3III,-5III,-6aIII,-6bIII, CH2Ph), 4.83 (d, 1 H, JA,B 10.9 Hz; A of AB quartet), 5.03-5.05 (m, 2 H; H-1I,-2II), 5.25-5.28 (m, 2 H; H-1II,-1III), 5.63 (dd, 1 H, J3,4=J4,5 9.9 Hz; H-4II), 5.77 (dd, 1 H, J1,2 2.0, J2,3 3.1 Hz; H-2″), 5.92 (dd, 1 H, J3,4 9.7, J4,5 9.9 Hz; H-4III), 6.99-7.62, 7.80-8.16 (2 m, 50 H; Ar).

Workup

  1. temperaturethe combined mixture was heated (70°, 60 min)
  2. customAfter the time, the solvents were evaporated

Sources & evidence

ORD record
ord-c8dcc3b3c0cf4fe682ac838054affac7
Source dataset
uspto-grants-2012_05
Patent number
US08173606B2

Reaction notes

Loading…