Triphenylphosphine → 6-[2-(1H-1-imidazolyl)ethoxy]-7-methyl-1,2,3,4-tetrahydro-1-naphthalenone

HRID 1859813

反応式

HRID 1859813 の反応式
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[CH3:12])[C:8](=[O:13])[CH2:7][CH2:6][CH2:5]2.[N:14]1([CH2:19][CH2:20]O)[CH:18]=[CH:17][N:16]=[CH:15]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1.CCOC(C)=O>[N:14]1([CH2:19][CH2:20][O:1][C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][C:11]=2[CH3:12])[C:8](=[O:13])[CH2:7][CH2:6][CH2:5]3)[CH:18]=[CH:17][N:16]=[CH:15]1

参加物

7

反応物 4

HCID 11776TriphenylphosphineHCID 74168N-(2-Hydroxyethyl)imidazoleHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 186264826-Hydroxy-7-methyl-1,2,3,4-tetrahydronaphthalen-1-one

生成物 1

HCID 186265056-[2-(1H-1-imidazolyl)ethoxy]-7-methyl-1,2,3,4-tetrahydro-1-naphthalenone収率 32.9%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

Under N2, a solution of 2.08 g (11.8 mmol) of 6-hydroxy-7-methyl-1,2,3,4-tetrahydro-1-naphthalenone in 25 mL of THF was treated with 1.46 g (13.9 mmol) of 2-(1H-1-imidazolyl)-1-ethanol and 3.1 g (11.8 mmol) of triphenylphosphine. The solution was cooled in ice and treated with a solution of 1.9 mL (11.8 mmol) of diethyl azodicarboxylate in 5 mL of THF. The solution was allowed to stir at room temperature overnight. The mixture was diluted with EtOAc and washed twice with H2O, twice with saturated NaHCO3, then with saturated NaCl. Drying over MgSO4 and removal of the solvent under pressure left the crude product. Chromatography on silica gel, eluting with CHCl3/MeOH (95/5) gave the product which was recrystallized from EtOAc/hexane to give 1.05 g (32.9% yield) of the product as a tan solid, mp 118-120° C. The structure was confirmed by NMR and mass spectroscopy. MS m/z 271 (M+H+).

後処理

  1. temperatureThe solution was cooled in ice
  2. washwashed twice with H2O, twice with saturated NaHCO3
  3. dry with materialDrying over MgSO4 and removal of the solvent under pressure
  4. waitleft the crude product
  5. washChromatography on silica gel, eluting with CHCl3/MeOH (95/5)
  6. customgave the product which
  7. customwas recrystallized from EtOAc/hexane

出典と根拠

ORDレコード
ord-69e959bd507e469e8af7543fe62aa513
出典データセット
uspto-grants-2003_03
特許番号
US06528535B2

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