Methyl Thioglycolate → HCID 54697144, compound

HRID 621787Notes

Reaction equation

HRID 621787 reaction equation
[CH:1]([CH:4]([C:10]([CH3:12])=O)[C:5](OCC)=[O:6])([CH3:3])[CH3:2].[C:13]([O:17][CH3:18])(=[O:16])[CH2:14][SH:15].[Na]>>[OH:6][C:5]1[C:4]([CH:1]([CH3:3])[CH3:2])=[C:10]([CH3:12])[S:15][C:14]=1[C:13]([O:17][CH3:18])=[O:16]

Participants

4

Reactant 3

HCID 16907Methyl ThioglycolateHCID 95544Butanoic acid, 2-acetyl-3-methyl-, ethyl esterHCID 5360545Sodium

Product 1

HCID 54697144HCID 54697144, compound

Procedure

Prepared by the method described in Example 1 from ethyl α-isopropylacetoacetate (prepared by the procedure of Manuel and Hagen, Org. Syn., 7, 248 (1951)) (12 g, 70 mmoles), methyl thioglycolate (15.7 g, 140 mmoles) and sodium (3.2 g, 139 mmoles). The product is extracted with CH2Cl2 twice. The combined extracts are washed with aqueous NaCl twice, dried over MgSO4 and stripped of solvent under reduced pressure. Distillation of the residue gave the product (3.3 g); bp 68°-71° C. (0.3 mmHg).

Workup

  1. customPrepared by the method
  2. customprepared by the procedure of Manuel and Hagen, Org
  3. extractionThe product is extracted with CH2Cl2 twice
  4. washThe combined extracts are washed with aqueous NaCl twice
  5. dry with materialdried over MgSO4
  6. distillationDistillation of the residue

Sources & evidence

ORD record
ord-c2fd756dd2f146098f35ef3bec0c90e3
Source dataset
uspto-grants-1989_04
Patent number
US04824958

Reaction notes

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