Acetic Anhydride → HCID 12414551, compound

HRID 2163667Notes

Reaction equation

HRID 2163667 reaction equation
[Cl:1][C:2]1[CH:23]=[CH:22][CH:21]=[CH:20][C:3]=1[CH2:4][N:5]1[CH2:10][CH2:9][C:8]2[S:11][C:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:13]([OH:14])[C:7]=2[CH2:6]1.[C:24](OC(=O)C)(=[O:26])[CH3:25]>>[C:24]([O:14][C:13]1[C:7]2[CH2:6][N:5]([CH2:4][C:3]3[CH:20]=[CH:21][CH:22]=[CH:23][C:2]=3[Cl:1])[CH2:10][CH2:9][C:8]=2[S:11][C:12]=1[C:15]([O:17][CH2:18][CH3:19])=[O:16])(=[O:26])[CH3:25]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 54729700HCID 54729700, compound

Product 1

HCID 12414551HCID 12414551, compound

Procedure

A solution of 5-o-chlorobenzyl-2-ethoxycarbonyl-3-hydroxy-4,5,6,7-tetrahydro-thieno[3,2-c]pyridine (35.3 g; 0.1 mole) in acetic anhydride (200 cc) is refluxed during one hour, under a nitrogen atmosphere. The reaction mixture is then evaporated to dryness and the residue is dissolved in ether. The organic phase is washed with water, dried over anhydrous sodium sulfate, treated with vegetable charcoal, filtered and evaporated in vacuo. The resulting pale yellow crystals are recrystallized from cyclohexane; M.p. = 110° C; Yield: 31.9 g (80%).

Workup

  1. customThe reaction mixture is then evaporated to dryness
  2. dissolutionthe residue is dissolved in ether
  3. washThe organic phase is washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. additiontreated with vegetable charcoal
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customThe resulting pale yellow crystals are recrystallized from cyclohexane

Sources & evidence

ORD record
ord-29df7d9eadb34addb7fc77a6bae34b1c
Source dataset
uspto-grants-1979_01
Patent number
US04136186

Reaction notes

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