KBS16-2 - Azidation of ferrocenylmethanol

KlementineJBS / USYD_PhD_ELN

This repository forms the electronic laboratory notebook (ELN)for Klementine Burrell-Sander's PhD's

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Closed KlementineJBS closed 2 years ago

KlementineJBS commented 2 years ago

Reaction Scheme

Bromoadamantane to azidoadamantane (ELN)

Outcome

49 mg (0.204 mmol), 45%

TLC indicated reaction completion - is low yield due to loss during purification?

KlementineJBS commented 2 years ago

set up flask and added KBS15 (98.6 mg, 0.456 mmol) by solution transfer (5 mL dry THF)
added DBU (68 μL, 0.456 mmol, 1 equiv.) and DPPA (117 μL, 0.547 mmol, 1.2 equiv.)
left at 12 pm (rt)
at 3pm, heated to 50 C

KlementineJBS commented 2 years ago

added extra DBU (34 μL, 0.228 mmol) and DPPA (58 μL, 0.274 mmol) at 10.30 am and increased heat to 60 C
TLC'd at 4.30pm and quenched with water (20 mL)
extracted with toluene (3 x 30 mL) and washed with brine (40 mL)

$TLC of fractions$

KlementineJBS commented 2 years ago

Columned according to literature method. Compounds in fractions 2, 3 and 4 - combined 2 and 3 and rotovapped down.

$fractions TLC$

Vial (empty): 15.7133 g

NMR suggested product was formed (matches literature values).

1H NMR (300 MHz, Chloroform-d) δ 4.24 (m, 2H), 4.20 (m, 2H), 4.17 (s, 5H), 4.12 (s, 2H).