1,2-Dichlorobenzene → HCID 118391137, compound

HRID 1055606Notes

Reaction equation

HRID 1055606 reaction equation
C([O:8][C@H:9]1[C@H:15]([O:16]CC2C=CC=CC=2)[C@@H:14]([O:24]CC2C=CC=CC=2)[C@:13]2([C:33]3[CH:38]=[CH:37][C:36]([Cl:39])=[C:35]([CH2:40][C:41]4[CH:46]=[CH:45][C:44]([O:47]CC5C=CC=CC=5)=[CH:43][CH:42]=4)[CH:34]=3)[O:32][C@@:10]1([C:55]([OH:58])([CH3:57])[CH3:56])[CH2:11][O:12]2)C1C=CC=CC=1.ClC1C=CC=CC=1Cl>[Pd].CO.O1CCCC1>[Cl:39][C:36]1[CH:37]=[CH:38][C:33]([C@@:13]23[O:32][C@@:10]([C:55]([OH:58])([CH3:57])[CH3:56])([CH2:11][O:12]2)[C@@H:9]([OH:8])[C@H:15]([OH:16])[C@H:14]3[OH:24])=[CH:34][C:35]=1[CH2:40][C:41]1[CH:42]=[CH:43][C:44]([OH:47])=[CH:45][CH:46]=1

Participants

5

Reactant 2

HCID 72391,2-DichlorobenzeneHCID 131736402HCID 131736402, compound

Product 1

HCID 118391137HCID 118391137, compoundYield 104.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of 2-[(1S,2S,3S,4R,5S)-2,3,4-tribenzyloxy-5-[3-[(4-benzyloxyphenyl)methyl]-4-chloro-phenyl]-6,8-dioxabicyclo[3.2.1]octan-1-yl]propan-2-ol 25o (100 mg, 0.12 mmol) in a methanol/tetrahydrofuran mixture (v/v=4/1, 10 mL) were added o-dichlorobenzene (0.07 mL, 0.63 mmol) and 10% Pd/C (20 mg, 0.02 mmol) at room temperature. The mixture was stirred under H2 at room temperature for 4 hours and filtered. The filtrate was concentrated in vacuo to give the title compound 25p as a white solid (54.8 mg, 100%). The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 481.0[M+HCOO]−.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-8039ce689f924715a0dd536511bb8f47
Source dataset
uspto-grants-2016_07
Patent number
US09394329B2

Reaction notes

Loading…