Acetic Anhydride → HCID 21406425, compound

HRID 972245Notes

Reaction equation

HRID 972245 reaction equation
[CH3:1][C:2]1[S:3][C:4](/[CH:17]=[CH:18]/[CH:19]([OH:25])[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[C:5]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])[N:6]=1.[C:26](OC(=O)C)(=[O:28])[CH3:27]>N1C=CC=CC=1.O>[CH3:1][C:2]1[S:3][C:4](/[CH:17]=[CH:18]/[CH:19]([O:25][C:26](=[O:28])[CH3:27])[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[C:5]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])[N:6]=1

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 21406422HCID 21406422, compound

Product 1

HCID 21406425HCID 21406425, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

To the solution of 367 mg of 2-methyl-4-(6-carbomethoxy-hexyl)-5-(3-hydroxy-1-trans-octenyl)-thiazole (Ic, R1 = CH3) in 4 ml of anhydrous pyridine, 1 ml of acetic anhydride was added. The reaction mixture was allowed to stand for 24 hours at room temperature, diluted with 50 ml of water and extracted with 3 × 15 ml of ethyl acetate. The ethyl acetate extract was washed with water, dried over sodium sulphate and evaporated in vacuo. The obtained 403 mg of evaporation residue was purified by preparative thin layer chromatography, using a silica gel layer as adsorbent and a mixture of 40 % ethyl acetate and 60 % n-heptane as running solvent. Thus, 290 mg of 2-methyl-4-(6-carbomethoxyhexyl)-5-(3-acetoxy-1-trans-octenyl)-thiazole (Ie, R1 = CH3) of chromatographic purity were obtained.

Workup

  1. extractionextracted with 3 × 15 ml of ethyl acetate
  2. extractionThe ethyl acetate extract
  3. washwas washed with water
  4. dry with materialdried over sodium sulphate
  5. customevaporated in vacuo
  6. customThe obtained 403 mg of evaporation residue
  7. customwas purified by preparative thin layer chromatography
  8. additiona mixture of 40 % ethyl acetate and 60 % n-heptane

Sources & evidence

ORD record
ord-c4fb06d90b814dc789e7c7fa136b7ab4
Source dataset
uspto-grants-1977_10
Patent number
US04052407

Reaction notes

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