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

HRID 1278841
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HRID 1278841 반응식
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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

10

반응물 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

생성물 1

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

시약·촉매·용매 4

HCID 62652Cuprous chloride촉매HCID 887Methanol용매2회HCID 962Water용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-0627d8b6b177464989eb15fb45861a70
출처 데이터셋
uspto-grants-2002_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06444709B1

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