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Benzoyl chloride → 2-(Benzhydrylidene-amino)-2-benzoyl-hex-5-enoic acid tert-butyl ester

HRID 579525
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 579525
[C:1]([O:5][C:6](=[O:26])[CH:7]([N:12]=[C:13]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:8][CH2:9][CH:10]=[CH2:11])([CH3:4])([CH3:3])[CH3:2].C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[C:37](Cl)(=[O:44])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>C1COCC1>[C:1]([O:5][C:6](=[O:26])[C:7]([N:12]=[C:13]([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)([C:37](=[O:44])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[CH2:8][CH2:9][CH:10]=[CH2:11])([CH3:2])([CH3:3])[CH3:4]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 7412Benzoyl chlorideHCID 2724254Sodium bis(trimethylsilyl)amideHCID 160669741,1-Dimethylethyl 2-[(diphenylmethylene)amino]-5-hexenoate

Produkt 1

HCID 866637242-(Benzhydrylidene-amino)-2-benzoyl-hex-5-enoic acid tert-butyl esterAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel

Versuchsvorschrift

A solution of 2-(benzhydrylidene-amino)-hex-5-enoic acid tert-butyl ester (350 mg, 1 mmol) in THF (5 mL, 0.2 M) was cooled to −78° C. and treated with sodium bis(trimethylsilyl)amide (2.2 mL, 1.0 M, 2.2 equiv) drop wise over 5 min and stirred for 30 min. After adding benzoyl chloride (140 μl, 1.2 mmol, 1.2 eq), the reaction mixture was warmed up to room temperature and stirred for an additional 1.5 h. The solution was cooled to 0° C. and quenched with water (5 mL). The resulting solution was diluted with ethyl acetate and washed successively with water and saturated aqueous NaCl, dried over MgSO4, filtered and concentrated. Purification by MPLC (1-40% ethyl acetate in heptane gave 2-(benzhydrylidene-amino)-2-benzoyl-hex-5-enoic acid tert-butyl ester (477 mg, 1 mmol, 100%).

Aufarbeitung

  1. stirringstirred for an additional 1.5 h
  2. temperatureThe solution was cooled to 0° C.
  3. customquenched with water (5 mL)
  4. additionThe resulting solution was diluted with ethyl acetate
  5. washwashed successively with water and saturated aqueous NaCl
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customPurification by MPLC (1-40% ethyl acetate in heptane

Quellen und Nachweise

ORD-Eintrag
ord-b217d9585daf41bb84cf645283863799
Quelldatensatz
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09040703B2

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