Water → Methyl-2-o-acetyl-3,5-bis-o-(2,4-dichlorobenzyl)-1-o-methyl-d-ribofuranose

HRID 1865786Notes

Reaction equation

HRID 1865786 reaction equation
[CH3:1][C:2]1([O:19][C@H:18]([CH2:20][O:21][CH2:22][C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][C:24]=2[Cl:30])[C@@H:7]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=2[Cl:17])[C@H:5]1[OH:6])[O:3][CH3:4].[CH3:31][C:32](OC(C)=O)=[O:33].O>N1C=CC=CC=1.CN(C1C=CN=CC=1)C>[CH3:1][C:2]1([O:19][C@H:18]([CH2:20][O:21][CH2:22][C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][C:24]=2[Cl:30])[C@@H:7]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=2[Cl:17])[C@H:5]1[O:6][C:32](=[O:33])[CH3:31])[O:3][CH3:4]

Participants

6

Reactant 3

HCID 962WaterHCID 7918Acetic AnhydrideHCID 69036486Methyl-3,5-bis-o-(2,4-dichlorobenzyl)-1-o-methyl-d-ribofuranose

Product 1

HCID 69037254Methyl-2-o-acetyl-3,5-bis-o-(2,4-dichlorobenzyl)-1-o-methyl-d-ribofuranose

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

To the solution of raw oil from Step 2 above (173.6 g, 0.3600 mol) in 1.379 L pyridine, were added Ac2O (33.970 mL, 0.3600 mol) and DMAP (1.3766 g, 0.01127 mol). After 21 hours of stirring at room temperature 1.4 L H2O were added. The solution was acidified with 1.45 L concentrated HCL. The acidified product was extracted with EtOAc, dried with MgSO4 and concentrated in vacuo. The residue was isolated as 85.75 g (0.1636 mol) of clear oil.

Workup

  1. additionwere added
  2. concentrationconcentrated HCL
  3. extractionThe acidified product was extracted with EtOAc
  4. dry with materialdried with MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-68c46821cf6149e397261a66c3f7e662
Source dataset
uspto-grants-2009_12
Patent number
US07629320B2

Reaction notes

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