Sodium Methoxide → HCID 11030841, compound

HRID 582891Notes

Reaction equation

HRID 582891 reaction equation
Cl[CH:2]([C@H:7]([OH:15])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[C:3]([O:5][CH3:6])=[O:4].C[O-].[Na+]>CO>[O:15]1[C@H:7]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[C@H:2]1[C:3]([O:5][CH3:6])=[O:4]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 54438084HCID 54438084, compound2×

Product 1

HCID 11030841HCID 11030841, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Procedure

To 500 ml of a methanol solution of 90 g (0.384 mol) of the methyl (3R)-2-chloro-3-hydroxydecanoate (VIII) obtained in (2) above was added dropwise 78 g (0.4 mol) of a 28% methanol solution of sodium methoxide at 0 to 5° C., followed by stirring at room temperature for 1 hour. After confirming disappearance of the methyl (3R)-2-chloro-3-hydroxydecanoate (VIII) by TLC, methanol was evaporated. The concentrate was cooled, adjusted to pH 8 to 9 with 500 ml of a phosphate buffer (prepared by dissolving 5.55 g of sodium dihydrogen phosphate (NaH2PO4.2H2O) and 21.5 g of sodium hydrogenphosphate (Na2HPO4.12H2O) in 1 l of water), and extracted with 1 of isopropyl ether. The isopropyl ether was evaporated, and the residue was distilled to obtain 65.3 g (0.326 mol; yield: 85.0%) of the title compound (V-1) (boiling point: 135° C./0.3 mmHg).

Workup

  1. customwas evaporated
  2. temperatureThe concentrate was cooled
  3. extractionextracted with 1 of isopropyl ether
  4. customThe isopropyl ether was evaporated
  5. distillationthe residue was distilled

Sources & evidence

ORD record
ord-b6d5dcedad2a476f91abb5c6454f04ef
Source dataset
uspto-grants-1999_07
Patent number
US05925792

Reaction notes

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