Sodium Methoxide → HCID 56999066, compound

HRID 582899Notes

Reaction equation

HRID 582899 reaction equation
Cl[CH:2]([C@H:7]([OH:23])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[C:3]([O:5][CH3:6])=[O:4].ClC([C@H](O)CC)C(OC)=O.C[O-].[Na+]>CO>[O:23]1[C@H:7]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[C@H:2]1[C:3]([O:5][CH3:6])=[O:4]

Participants

5

Reactant 3

HCID 10942334Sodium MethoxideHCID 53719841HCID 53719841, compound2×HCID 54420244HCID 54420244, compound

Product 1

HCID 56999066HCID 56999066, compoundYield 70.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Procedure

To 1.3 l of methanol solution of 262 g (0.75 mol) of the methyl (3R)-2-chloro-3-hydroxyoctadecanoate (VIII) obtained in (2) above was added dropwise 150 g (0.777 mol) of a 28% methanol solution of sodium methoxide at 0 to 5° C. The mixture was stirred at room temperature for 1 hour. After confirming disappearance of the compound (VIII) by TLC, methanol was evaporated. The concentrate was cooled, adjusted to pH 8 to 9 with 1.2 l of a phosphate buffer, and extracted with 3 l of isopropyl ether. Isopropyl ether was evaporated, and the resulting crude crystals were recrystallized from heptane to give 165 g (0.529 mol; yield: 70.5%) of the title compound (V-1) (melting point: 54-55° C.).

Workup

  1. customwas evaporated
  2. temperatureThe concentrate was cooled
  3. extractionextracted with 3 l of isopropyl ether
  4. customIsopropyl ether was evaporated
  5. customthe resulting crude crystals were recrystallized from heptane

Sources & evidence

ORD record
ord-af88a1d66a2b49d5b05467189dbaa79c
Source dataset
uspto-grants-1999_07
Patent number
US05925792

Reaction notes

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