Sodium Methoxide → HCID 58681695, compound

HRID 2059561Notes

Reaction equation

HRID 2059561 reaction equation
[Cl:1][C:2]1[CH:31]=[C:30]([Cl:32])[CH:29]=[CH:28][C:3]=1[CH2:4][O:5][CH2:6][C@H:7]1[O:11][CH:10]([O:12][CH3:13])[C@H:9](CC([O-])=O)[C@H:8]1[O:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:21]=1[Cl:27].C[O-:34].[Na+]>CO>[Cl:1][C:2]1[CH:31]=[C:30]([Cl:32])[CH:29]=[CH:28][C:3]=1[CH2:4][O:5][CH2:6][C@H:7]1[O:11][CH:10]([O:12][CH3:13])[C@H:9]([OH:34])[C@@H:8]1[O:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:21]=1[Cl:27]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 86642241HCID 86642241, compound

Product 1

HCID 58681695HCID 58681695, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of (3R,4R,5R)-5-(2,4-dichloro-benzyloxymethyl)-4-(2,4-dichlorobenzyloxy)-2-methoxy-tetrahydrofuran-3-acetate I-1 (10 g, 19.1 mmol) in MeOH (150 ml) is added a solution of 30% NaOMe in MeOH (5.37 ml, 28.6 mmol, 1.5 equiv.) and the reaction is stirred at room temperature for 30 mins. The reaction mixture is concentrated and dissolved in ethyl acetate (180 ml), washed with 1 N HCl solution and saturated brine, dried (anhyd Na2SO4) and concentrated to give (3R,4S,5R)-5-(2,4-Dichlorobenzyloxymethyl)-4-(2,4-dichlorobenzyloxy)-2-methoxy-tetrahydrofuran-3-ol I-2 as yellowish oil. The obtained crude compound is used for the next step without further purification.

Workup

  1. concentrationThe reaction mixture is concentrated
  2. dissolutiondissolved in ethyl acetate (180 ml)
  3. washwashed with 1 N HCl solution and saturated brine
  4. dry with materialdried (anhyd Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-9401873432664ee79db02dfe3d817f3c
Source dataset
uspto-grants-2012_10
Patent number
US08278282B2

Reaction notes

Loading…