Triacetoxyperiodinane → 2-Formyl-2,3-dihydro-1H-indene-5-carbonitrile

HRID 1466040Notes

Reaction equation

[OH:1][CH2:2][CH:3]1[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:12]#[N:13])[CH:9]=2)[CH2:4]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[CH:2]([CH:3]1[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:12]#[N:13])[CH:9]=2)[CH2:4]1)=[O:1]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 2-(Hydroxymethyl)-2,3-dihydro-1H-indene-5-carbonitrile (3.7 g, 21 mmol) in 80 mL of DCM was added Dess-Martin reagent (18 g, 43 mmol) in one portion at 0° C. The mixture was stirred at 0° C. for 1 hour, and then stirred at rt. overnight. The reaction mixture was purified with column chromatography (EtOAc:PE=1:20) to obtain 2-Formyl-2,3-dihydro-1H-indene-5-carbonitrile. 1H-NMR (400 MHz, CDCl3) δ 9.77 (d, J=1.2 Hz, 1H), 7.45-7.51 (m, 2H), 7.32 (d, J=7.6 Hz, 1H), 3.32-3.40 (m, 3H), 3.18-3.25 (m, 2H).

Workup

stirringstirred at rt
customovernight
customThe reaction mixture was purified with column chromatography (EtOAc:PE=1:20)

Sources & evidence

ORD record: ord-870b834cc1304e269cb377a5c8b5d91e
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08999990B2

Reaction notes

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