Ethanethiol → 5-[Bis(ethylsulfanyl)methylidene]-2,2-dimethyl-1,3-dioxane-4,6-dione

HRID 464408ノート

反応式

HRID 464408 の反応式
CS[C:3]([S:14][CH3:15])=[C:4]1[C:9](=[O:10])[O:8][C:7]([CH3:12])([CH3:11])[O:6][C:5]1=[O:13].[CH2:16]([SH:18])[CH3:17].[CH3:19][O-].[Na+]>CO>[CH2:16]([S:18][C:3]([S:14][CH2:15][CH3:19])=[C:4]1[C:9](=[O:10])[O:8][C:7]([CH3:12])([CH3:11])[O:6][C:5]1=[O:13])[CH3:17]

参加物

5

反応物 3

HCID 6343EthanethiolHCID 17451285-[Bis(methylsulfanyl)methylidene]-2,2-dimethyl-1,3-dioxane-4,6-dioneHCID 10942334Sodium Methoxide

生成物 1

HCID 136798125-[Bis(ethylsulfanyl)methylidene]-2,2-dimethyl-1,3-dioxane-4,6-dione収率 23.2%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

A solution of 5-[bis(methylthio)methylene]-2,2-dimethyl-1,3-dioxane-4,6-dione (2.3 g, 9.2 mmole, described in example 3), ethanethiol (8.4 g, 10 mL, 135 mmole) and sodium methoxide (480 mg, 20.7 mmole) in dry methanol (12 mL) was stirred at 20°-22° C. for 30 min. The solution was poured into ice water. The resultant mixture was extracted with ethyl acetate. The combined extracts were washed with water, dried (MgSO4) and concentrated to dryness under reduced pressure. The residue was purified by HPLC (20% ethyl acetate in hexane, v/v). The purest fractions were combined. The solvent was removed under reduced pressure to give 0.59 g of the title compound as an oil; NMR (CDCl3) δ 1.36 (t, J=7 Hz, 6H), 1.72 (s, 6H), 3.11 (3t, J=7 Hz, 4H); IR (CHCl3) 1715 cm-1 ; UVλmax (MeOH) 345 nm (ε 13,040), 215 (8160).

後処理

  1. extractionThe resultant mixture was extracted with ethyl acetate
  2. washThe combined extracts were washed with water
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated to dryness under reduced pressure
  5. customThe residue was purified by HPLC (20% ethyl acetate in hexane, v/v)
  6. customThe solvent was removed under reduced pressure

出典と根拠

ORDレコード
ord-1e286971a61643f58f9db9924f333c58
出典データセット
uspto-grants-1985_10
特許番号
US04547516

反応ノート

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