Dimethylformamide → HCID 86209319、化合物

HRID 1815051ノート

反応式

HRID 1815051 の反応式
[O:1]=[S:2]1(=[O:11])[CH2:7][CH2:6][CH:5]([C:8](O)=[O:9])[CH2:4][CH2:3]1.CN(C=O)C.C(Cl)(=O)C(Cl)=O.[CH2:23]([O:25][C:26]#[CH:27])[CH3:24]>C(Cl)Cl.C1COCC1.C(N(CC)CC)C>[CH2:26]([O:25][C:23]1[C:5]2([CH2:6][CH2:7][S:2](=[O:11])(=[O:1])[CH2:3][CH2:4]2)[C:8](=[O:9])[CH:24]=1)[CH3:27]

参加物

8

反応物 4

HCID 6228DimethylformamideHCID 61239Ether, ethyl ethynylHCID 65578Oxalyl chlorideHCID 1491755Tetrahydro-2H-thiopyran-4-carboxylic acid 1,1-dioxide

生成物 1

HCID 86209319HCID 86209319、化合物収率 67%

試薬・触媒・溶媒 3

HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒HCID 8471Triethylamine溶媒

実験手順

A solution of 1,1-dioxo-hexahydro-1λ6-thiopyran-4-carboxylic acid (10.2 g, 57.3 mmol) [prepared according to the procedure of Org. Prep. Proc. Int. 1977, 94] and DMF (0.3 ml) in DCM (120 ml) at rt, was treated dropwise with oxalyl chloride and the resulting slurry stirred for 3d. The crude reaction was then concentrated in vacuo to give an oil which was re-dissolved in THF (100 ml), treated with ethoxyacetylene (10 ml, 50% w/w) and triethylamine (10 ml) and the resulting slurry stirred for 10d at rt. Filtration and concentration of the filtrate in vacuo gave a crude oil which was purified by chromatography (SiO2, 30% EtOAc:hexanes) to give the title compound as a yellow oil (8.9 g, 38.6 mmol, 67%). δH (CDCl3, 300K) 4.88 (1H, s), 4.27 (2H, q, J 7.1 Hz), 3.44-3.37 (2H, m), 3.13-3.05 (2H, m), 2.47-2.40 (2H, m), 2.35-2.29 (2H, m), 1.48 (3H, t, J 7.1 Hz); m/z (ES+, 70V) 230.9 (MH+).

後処理

  1. customThe crude reaction
  2. concentrationwas then concentrated in vacuo
  3. customto give an oil which
  4. filtrationFiltration and concentration of the filtrate in vacuo
  5. customgave a crude oil which
  6. customwas purified by chromatography (SiO2, 30% EtOAc:hexanes)

出典と根拠

ORDレコード
ord-6bad974257d448669f4ff32d4b9dfd94
出典データセット
uspto-grants-2005_04
特許番号
US06878718B2

反応ノート

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