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Benzyl Alcohol → phenylmethyl (2-methyl-2,3-dihydro-1H-inden-2-yl)carbamate

HRID 471813
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 471813
C[C:2]1([C:11](O)=O)[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3]1.C([N:16]([CH2:19]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:28])C=CC=CC=1.[CH2:38]([OH:45])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>C1C=CC=CC=1.Cl>[CH3:11][C:2]1([NH:16][C:19](=[O:28])[O:45][CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[CH2:3][C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH2:10]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 244Benzyl AlcoholHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 153388422-methyl-2,3-dihydro-1H-indene-2-carboxylic acid

Produkt 1

HCID 57585915phenylmethyl (2-methyl-2,3-dihydro-1H-inden-2-yl)carbamate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 241
Benzene
Lösungsmittel
HCID 313Hydrochloric AcidLösungsmittel

Versuchsvorschrift

To a solution of 2-methyl-2,3-dihydro-1H-indene-2-carboxylic acid (0.200 g, 1.14 mmol) and triethylamine (0.17 mL, 1.2 mmol) in benzene (2 mL) at 0° C. was added diphenyl phosphorylazide (0.257 g, 1.19 mmol). The mixture was stirred 15 min, benzyl alcohol (0.123 mL, 1.19 mmol) was added and the reaction was heated under reflux for 16 hours. Upon cooling, the mixture was diluted with 10% HCl and extracted with ethyl acetate (2×25 mL). Combined organics were washed with brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by flash chromatography (EtOAc/hexanes) affording the title compound. 1H NMR (400 MHz, CDCl3) δ ppm 1.55 (s, 3H), 2.98 (d, J=15.9 Hz, 2H), 3.28 (d, J=15.9 Hz, 2H), 7.12-7.18 (m, 4H), 7.29-7.37 (m, 5H).

Aufarbeitung

  1. temperaturethe reaction was heated
  2. temperatureunder reflux for 16 hours
  3. temperatureUpon cooling
  4. extractionextracted with ethyl acetate (2×25 mL)
  5. washCombined organics were washed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash chromatography (EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-97d76e7cca7144d0a2f8a285ad11e931
Quelldatensatz
uspto-grants-2014_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08633175B2

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