1,2-Dichlorobenzene → HCID 25154393, compound

HRID 1713595Notes

Reaction equation

HRID 1713595 reaction equation
C([O:8][C@@H:9]1[C@@H:14]([O:15]CC2C=CC=CC=2)[C@H:13]([O:23]CC2C=CC=CC=2)[C@@H:12]([CH2:31][O:32]CC2C=CC=CC=2)[O:11][C@:10]21[C:43]1[CH:44]=[C:45]([CH2:49][C:50]3[CH:55]=[CH:54][C:53]([CH2:56][CH3:57])=[CH:52][CH:51]=3)[C:46]([Cl:48])=[CH:47][C:42]=1[O:41][CH2:40]2)C1C=CC=CC=1.ClC1C=CC=CC=1Cl.[H][H]>CO.C1COCC1.[OH-].[OH-].[Pd+2]>[Cl:48][C:46]1[C:45]([CH2:49][C:50]2[CH:51]=[CH:52][C:53]([CH2:56][CH3:57])=[CH:54][CH:55]=2)=[CH:44][C:43]2[C@@:10]3([CH2:40][O:41][C:42]=2[CH:47]=1)[C@H:9]([OH:8])[C@@H:14]([OH:15])[C@H:13]([OH:23])[C@@H:12]([CH2:31][OH:32])[O:11]3

Participants

7

Reactant 3

HCID 72391,2-DichlorobenzeneHCID 86621848HCID 86621848, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 25154393HCID 25154393, compoundYield 71.2%

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 29 (60 mg, 0.77 mmol) in a mixture of MeOH (2.4 mL) and THF (0.8 mL) were added Pd(OH)2/C (25 mg) and 1,2-dichlorobenzene (60 μL). A balloon of hydrogen gas was attached for 0.5 hours with vigorous stirring. LC/MS indicated that de-protection was complete. The reaction mixture was filtered through Celite, concentrated to a residue, and purified by preparatory TLC (5% MeOH in DCM) to give 30 (23 mg, 71.2%). 1H NMR (300 MHz, CD3OD) δ 7.18 (s, 1H), 7.07 (s, 4H), 6.82 (s, 1H), 4.68 (d, J=10.2 Hz, 1H), 4.59 (d, J=9.9 Hz, 1H), 3.99 (m, 2H), 3.59-3.80 (m, 3H), 3.28-3.37 (m, 3H), 2.58 (q, J=7.5 Hz, 2H), 1.19 (t, J=7.5 Hz, 3H).

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationconcentrated to a residue
  3. custompurified by preparatory TLC (5% MeOH in DCM)

Sources & evidence

ORD record
ord-7b1196da444e486689d4feefaa364bae
Source dataset
uspto-grants-2010_09
Patent number
US07795228B2

Reaction notes

Loading…