Hexanoic Acid → HCID 58256105, compound

HRID 1365618Notes

Reaction equation

HRID 1365618 reaction equation
[CH2:1]([O:3][C:4](=[O:14])[CH:5]([C:7]1[S:8][C:9]([Cl:13])=[C:10]([Cl:12])[CH:11]=1)O)[CH3:2].C[C:16](C)(C)[C:17]([O-:20])([O-])[O-:18].[C:23](O)(=O)CCCCC>C1C2C(CCCC2)CCC1>[CH2:1]([O:3][C:4](=[O:14])[CH2:5][C:7]1[S:8][C:9]([Cl:13])=[C:10]([Cl:12])[C:11]=1[CH2:16][C:17]([O:20][CH3:23])=[O:18])[CH3:2]

Participants

5

Reactant 3

HCID 8892Hexanoic Acid2×HCID 21927715TrimethylorthoacetateHCID 58256123HCID 58256123, compound

Product 1

HCID 58256105HCID 58256105, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 7044DecalinSolvent

Conditions

Temperature
180 °C

Procedure

A solution of the product from step (b) (12.2 g, 48.0 mmol) in decalin (145 ml) was treated with trimethylorthoacetate (24.5 ml, 192 mmol) and hexanoic acid (0.61 ml). The flask was equipped with a vigreux column and heated to 180° C. Additional hexanoic acid (3 ml) was periodically added over 6 h and the reaction was heated overnight. The reaction was concentrated on the rotavap and the residue was extracted with MeOH (100 ml ×2). The MeOH extracts were concentrated and purified by silica gel chromatography (EtOAc/Hexane-gradient) providing 4.36 g (29%) of the subtitle compound. MS: ESI (positive): 311, 313 (M+H).

Workup

  1. customThe flask was equipped with a vigreux column
  2. temperaturethe reaction was heated overnight
  3. concentrationThe reaction was concentrated on the rotavap
  4. extractionthe residue was extracted with MeOH (100 ml ×2)
  5. concentrationThe MeOH extracts were concentrated
  6. custompurified by silica gel chromatography (EtOAc/Hexane-gradient)

Sources & evidence

ORD record
ord-f672d1388b5a42ad886e1fc277b2ae3a
Source dataset
uspto-grants-2011_02
Patent number
US07893051B2

Reaction notes

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