HCID 86613970, compound → HCID 86613971, compound

HRID 254406Notes

Reaction equation

HRID 254406 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:44]([O:45][CH2:46][C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=3)[C@H:43]([O:53][CH2:54][C:55]3[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=3)[C@@H:42]([CH2:61][O:62][CH2:63][C:64]3[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=3)[O:41][C@@H:32]2[O:33][CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C@H:6]1[O:70][C:71](=[O:78])[C:72]1[CH:77]=[CH:76][CH:75]=[CH:74][CH:73]=1)C=C>CO.ClCCCl.Cl[Pd]Cl>[C:71]([O:70][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:44]([O:45][CH2:46][C:47]2[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=2)[C@H:43]([O:53][CH2:54][C:55]2[CH:56]=[CH:57][CH:58]=[CH:59][CH:60]=2)[C@@H:42]([CH2:61][O:62][CH2:63][C:64]2[CH:65]=[CH:66][CH:67]=[CH:68][CH:69]=2)[O:41][C@@H:32]1[O:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)(=[O:78])[C:72]1[CH:77]=[CH:76][CH:75]=[CH:74][CH:73]=1

Participants

5

Reactant 1

HCID 86613970HCID 86613970, compound

Product 1

HCID 86613971HCID 86613971, compoundYield 97.5%

Reagents, catalysts & solvents 3

HCID 24290Palladium ChlorideCatalystHCID 111,2-DichloroethaneSolventHCID 887MethanolSolvent

Procedure

PdCl2 (40 mg) was added to a solution of the allyl ether (24) (1.09 g, 0.97 mmol) in MeOH (10 mL) and 1,2-DCE (10 mL) and the combined mixture was heated (70°, 40 min). After the time, the solvents were evaporated and the residue subjected to FC (20-30% EtOAc/hexanes) to yield the alcohol (25) as a colourless oil (0.96 g, 91%). 1H NMR (CDCl3) δ 3.68-3.81, 3.97-4.06, 4.32-4.71 (3 m, 18H; H-2I,-3I,-4I,-5I,-6aI,-6bI,-3II,-5II,-6aII,-6bII, CH2Ph), 4.84 (d, 1H, JA,B 12 Hz; A of AB quartet), 5.05 (d, 1H, J1,2 1.9 Hz; H-1I), 5.26 (d, 1H; J1,2 1.9 Ha; H-1II), 5.61 (dd, 1H, J2,3 3.3 Hz; H-2II), 5.67 (dd, 1H, J3,4 9.8, J4,5 9.9 Hz; H-4II), 7.13-7.40, 7.48-7.59, 7.98-8.06 (3 m, 35H; Ar). 13C NMR (CDCl3) δ 60.61, 63.32 (2 C; C-6I,-6II), 69.06, 69.12, 69.25, 69.44, 70.45, 72.14, 72.65, 72.77, 73.48, 74.79, 75.48, 75.47, 76.23 (13 C; C-3I,-4I,-5I,-2II,-3II,-4II,-5II, OCH2, CH2Ph), 79.66 (C-2I), 98.34, 99.40 (C-1I,-1II), 127.70-138.47 (42 C; Ar), 165.97, 166.36, 166.97 (3 C; C═O).

Workup

  1. temperaturethe combined mixture was heated (70°, 40 min)
  2. customAfter the time, the solvents were evaporated

Sources & evidence

ORD record
ord-2db91d091a1f455c82bc03765e785210
Source dataset
uspto-grants-2011_01
Patent number
US07875592B2

Reaction notes

Loading…