Diethyl [chloro(4-methylphenyl)methyl]phosphonate → (5,6,7,8-Tetrahydro-3-methoxy-5,5,8,8-tetramethylnaphth-2-yl)-(4-tolyl)-acetylene

HRID 893743

Reaktionsgleichung

Reaktionsgleichung von HRID 893743
Cl[CH:2](P(=O)(OCC)OCC)[C:3]1[CH:8]=[CH:7][C:6]([CH3:9])=[CH:5][CH:4]=1.[CH:18]([C:20]1[C:29]([O:30][CH3:31])=[CH:28][C:27]2[C:26]([CH3:33])([CH3:32])[CH2:25][CH2:24][C:23]([CH3:35])([CH3:34])[C:22]=2[CH:21]=1)=O>CS(C)=O>[CH3:31][O:30][C:29]1[C:20]([C:18]#[C:2][C:3]2[CH:4]=[CH:5][C:6]([CH3:9])=[CH:7][CH:8]=2)=[CH:21][C:22]2[C:23]([CH3:35])([CH3:34])[CH2:24][CH2:25][C:26]([CH3:32])([CH3:33])[C:27]=2[CH:28]=1

Komponenten

4

Edukt 2

HCID 13604830Diethyl [chloro(4-methylphenyl)methyl]phosphonateHCID 147265222-Formyl-5,6,7,8-tetrahydro-3-methoxy-5,5,8,8tetramethylnaphthalene

Produkt 1

HCID 13604827(5,6,7,8-Tetrahydro-3-methoxy-5,5,8,8-tetramethylnaphth-2-yl)-(4-tolyl)-acetyleneAusbeute 51 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel2×

Versuchsvorschrift

A solution of 20.2 g (0.18 mole) of potassium tert.-butylate in 45 ml of dimethyl sulfoxide was added dropwise to a solution of 23.2 g (0.09 mole) of diethyl 1-chloro-1-(4-tolyl)-methylphosphonate and 22.1 g (0.09 mole) of 2-formyl-5,6,7,8-tetrahydro-3-methoxy-5,5,8,8-tetramethylnaphthalene in 270 ml of dry dimethyl sulfoxide at room temperature. The mixture was stirred for 30 minutes, poured onto 1 liter of ice water and extracted three times with ether. The ether phase was washed twice with water, dried over sodium sulfate and evaporated down to give 22.6 g (76%) of a slightly impure product. Recrystallization from methanol gave 15.2 g (51%) of the pure title compound of melting point 127° C.

Aufarbeitung

  1. extractionextracted three times with ether
  2. washThe ether phase was washed twice with water
  3. dry with materialdried over sodium sulfate
  4. customevaporated down
  5. customto give 22.6 g (76%) of a slightly impure product
  6. customRecrystallization from methanol

Quellen und Nachweise

ORD-Eintrag
ord-5f4276469eff49e2a5bbc4f25230fef2
Quelldatensatz
uspto-grants-1992_06
Patentnummer
US05126371

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