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Hydrochloric Acid → Methyl 3-oxo-3-(1,3-thiazol-2-yl)propanoate

HRID 39710
ノート
印刷プレビュー

反応式

HRID 39710 の反応式
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6](=[O:8])[CH3:7].[C:9](=O)([O:12]C)[O:10][CH3:11].[H-].[Na+].Cl>C(OCC)(=O)C.O.O1CCCC1>[O:8]=[C:6]([C:2]1[S:1][CH:5]=[CH:4][N:3]=1)[CH2:7][C:9]([O:10][CH3:11])=[O:12]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 12021Dimethyl CarbonateHCID 24758Sodium hydride2 回HCID 5201082-Acetylthiazole

生成物 1

HCID 57436906Methyl 3-oxo-3-(1,3-thiazol-2-yl)propanoate

試薬・触媒・溶媒 3

HCID 962Water溶媒
HCID 8028
Tetrahydrofuran
溶媒
HCID 8857Ethyl Acetate溶媒

実験手順

To 50 mL of a tetrahydrofuran solution containing 5.0 g of 1-(1,3-thiazol-2-yl)ethanone, 6.3 mL of dimethyl carbonate and 3.0 g of 60% sodium hydride were added at 10° C. The temperature of the reaction mixture was increased to room temperature, and the mixture was stirred for 16 hours. Thereto was further added 0.75 g of 60% sodium hydride, and the mixture was stirred for 4 hours. Water and ethyl acetate were then added thereto, and the reaction mixture was adjusted to pH 3.0 with 6 mol/L hydrochloric acid. The organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The organic layer and the extract were combined, the resultant solution was washed with an aqueous saturated sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue thus obtained was purified by silica gel column chromatography [eluent; hexane:ethyl acetate=5:1] to obtain 2.3 g of a yellow oily substance, methyl 3-oxo-3-(1,3-thiazol-2-yl)propionate.

後処理

  1. additionwere added at 10° C
  2. stirringthe mixture was stirred for 4 hours
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with ethyl acetate
  5. washthe resultant solution was washed with an aqueous saturated sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was removed under reduced pressure
  8. customThe residue thus obtained
  9. customwas purified by silica gel column chromatography [eluent; hexane:ethyl acetate=5:1]

出典と根拠

ORDレコード
ord-9bc99bf9eb234b0e900278f272f508e6
出典データセット
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08524738B2

反応ノート

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