Homoallyl bromide → 1,1-Dimethylethyl 2-[(diphenylmethylene)amino]-5-hexenoate

HRID 579521

Reaktionsgleichung

Reaktionsgleichung von HRID 579521
[C:1]([O:5][C:6](=[O:22])[CH2:7][N:8]=[C:9]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([CH3:4])([CH3:3])[CH3:2].C[Si]([N-][Si](C)(C)C)(C)C.[Na+].Br[CH2:34][CH2:35][CH:36]=[CH2:37]>C1COCC1>[C:1]([O:5][C:6](=[O:22])[CH:7]([N:8]=[C:9]([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[CH2:37][CH2:36][CH:35]=[CH2:34])([CH3:4])([CH3:2])[CH3:3]

Komponenten

5

Edukt 3

HCID 21241Homoallyl bromideHCID 688171N-(Diphenylmethylene)glycine tert-butyl esterHCID 2724254Sodium bis(trimethylsilyl)amide

Produkt 1

HCID 160669741,1-Dimethylethyl 2-[(diphenylmethylene)amino]-5-hexenoateAusbeute 94,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

While under a nitrogen atmosphere a stirred solution of (benzhydrylidene-amino)-acetic acid tert-butyl ester (5 g, 16.9 mmol) in THF (80 mL, 0.2 M) was carefully treated with sodium bis(trimethylsilyl)amide (18.6 mL, 1.0 M, 1.1 equiv) at −78° C. After stirring for 30 min, 4-bromo-but-1-ene (2.1 mL, 20.3 mmol, 1.2 equiv) was slowly added. The cooling bath was removed and the reaction mixture gradually warmed to room temperature and stirred for overnight. The solution was cooled to 0° C. and quenched with water. 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 (1-25% ethyl acetate in heptane) gave 2-(benzhydrylidene-amino)-hex-5-enoic acid tert-butyl ester as colorless oil (5.6 g, 15.9 mmol, 94%).

Aufarbeitung

  1. customThe cooling bath was removed
  2. stirringstirred for overnight
  3. temperatureThe solution was cooled to 0° C.
  4. customquenched with water
  5. additionThe resulting solution was diluted with ethyl acetate
  6. washwashed successively with water and saturated aqueous NaCl
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customPurification by MPLC (1-25% ethyl acetate in heptane)

Quellen und Nachweise

ORD-Eintrag
ord-1a24c120d9d042f78e7613297ca80e5d
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09040703B2

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