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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
Notes
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Reaction equation

HRID 1278841 reaction equation
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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

10

Reactant 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

Product 1

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

Reagents, catalysts & solvents 4

HCID 62652Cuprous chlorideCatalystHCID 887MethanolSolvent2×HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-0627d8b6b177464989eb15fb45861a70
Source dataset
uspto-grants-2002_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06444709B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes