Sodium Methoxide → HCID 58592574, compound

HRID 1944077Notes

Reaction equation

HRID 1944077 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[C@H:13]([OH:14])[C@@H:12]([OH:15])[C@H:11]([OH:16])[C@@H:10]([CH2:17]I)[O:9]2)=[CH:4][C:3]=1[CH2:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH3:28])=[CH:22][CH:21]=1.C[O-].[Na+]>CO.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[C@H:13]([OH:14])[C@@H:12]([OH:15])[C@H:11]([OH:16])[C:10](=[CH2:17])[O:9]2)=[CH:4][C:3]=1[CH2:19][C:20]1[CH:21]=[CH:22][C:23]([O:26][CH2:27][CH3:28])=[CH:24][CH:25]=1

Participants

5

Reactant 2

HCID 10942334Sodium MethoxideHCID 58436540HCID 58436540, compound

Product 1

HCID 58592574HCID 58592574, compoundYield 84.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
45 °C

Procedure

To a solution of (2S,3R,4R,5S,6S)-2-[4-chloro-3-(4-ethoxy-benzyl)-phenyl]-6-iodomethyl-tetrahydro-pyran-3,4,5-triol (2.5 g, 4.82 mmole) in dry methanol (20 mL), sodium methoxide (2.58 g, 48.2 mmole) was added at 0° C. and stirred at 45° C. for 18 hours. The reaction mixture was diluted with water (50 mL) and extracted with DCM (2×200 mL). The crude product was purified by silica gel column chromatography (1% methanol in DCM) to furnish 1.6 g of (2S,3R,4R,5S)-2-[4-chloro-3-(4-ethoxy-benzyl)-phenyl]-6-methylene-tetrahydro-pyran-3,4,5-triol.

Workup

  1. extractionextracted with DCM (2×200 mL)
  2. customThe crude product was purified by silica gel column chromatography (1% methanol in DCM)

Sources & evidence

ORD record
ord-8e2f901706654a918958e8e759dc386f
Source dataset
uspto-grants-2013_03
Patent number
US08394772B2

Reaction notes

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