Ethylamine → Methyl 5-(3,5,5,8,8-Pentamethyl-5,6,7,8-tetrahydronaphthalen-2-ylsulphonyl)penta-2,4-diynoate

HRID 1278841

反応式

HRID 1278841 の反応式
C(N)C.Br[C:5]#[C:6][C:7]([O:9][CH3:10])=[O:8].Cl.NO.[C:14]([S:16]([C:19]1[CH:20]=[C:21]2[C:26](=[CH:27][C:28]=1[CH3:29])[C:25]([CH3:31])([CH3:30])[CH2:24][CH2:23][C:22]2([CH3:33])[CH3:32])(=[O:18])=[O:17])#[CH:15].[Cl-].[NH4+]>O.CO.[Cu]Cl.C(OCC)(=O)C>[CH3:29][C:28]1[C:19]([S:16]([C:14]#[C:15][C:5]#[C:6][C:7]([O:9][CH3:10])=[O:8])(=[O:18])=[O:17])=[CH:20][C:21]2[C:22]([CH3:33])([CH3:32])[CH2:23][CH2:24][C:25]([CH3:30])([CH3:31])[C:26]=2[CH:27]=1

参加物

10

反応物 5

HCID 6341EthylamineHCID 25517Ammonium ChlorideHCID 294619Methyl 3-bromoprop-2-ynoateHCID 443297Hydroxyamine hydrochlorideHCID 223478256-Ethynylsulphonyl-1,1,4,4,7-pentamethyl-1,2,3,4-tetrahydronaphthalene

生成物 1

HCID 22347861Methyl 5-(3,5,5,8,8-Pentamethyl-5,6,7,8-tetrahydronaphthalen-2-ylsulphonyl)penta-2,4-diynoate

試薬・触媒・溶媒 4

HCID 62652Cuprous chloride触媒HCID 887Methanol溶媒2 回HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A 70% solution of ethylamine in water (563 μl) is added dropwise to a mixture of methyl 3-bromopropynoate (632 mg, 2.88 mmol), hydroxylamine hydrochloride (162 mg, 2.33 mmol) and copper (I) chloride (10 mg) in methanol. A solution of 6-ethynylsulphonyl-1,1,4,4,7-pentamethyl-1,2,3,4-tetrahydronaphthalene (Example 7(b)) (500 mg, 1.94 mmol) in methanol (5 ml) is then added dropwise. The reaction medium is stirred for 15 h at room temperature and treated with saturated aqueous ammonium chloride solution and ethyl acetate. The organic phase is washed with water, dried over magnesium sulphate and concentrated. The product is obtained in the form of an oil after purification by flash chromatography on silica (80/20 heptane/CH2Cl2). 1H NMR/CDCl3: 1.26 to 1.28 (s, 12H); 1.67 (s, 4H); 2.35 (s, 3H); 3.78 (s, 3H); 7.14 (s, 1H); 7.48 (s, 1H); 13C NMR/CDCl3: 19.7; CH3/31.8; 4*CH3/34.1; Cq/34.3; Cq/34.9; 2*CH2/52.9; CH3/71.7; CH/72.1; CH/80.2; Cq/124.5; Cq/127.6; Cq/12.8.3; CH/129.3; CH/134.8; Cq/144.6; Cq/146.2; Cq/153.4; Cq.

後処理

  1. washThe organic phase is washed with water
  2. dry with materialdried over magnesium sulphate
  3. concentrationconcentrated
  4. customThe product is obtained in the form of an oil
  5. customafter purification by flash chromatography on silica (80/20 heptane/CH2Cl2)

出典と根拠

ORDレコード
ord-0627d8b6b177464989eb15fb45861a70
出典データセット
uspto-grants-2002_09
特許番号
US06444709B1

関連ノート

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