Diethyl Ether → HCID 22609695, compound

HRID 2306554Notes

Reaction equation

[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:18]#N)[CH:15]3[CH2:16][CH:11]4[CH2:12][CH:13]([CH2:17][CH:9]2[CH2:10]4)[CH2:14]3)=[CH:4][CH:3]=1.[H-].C([Al+]CC(C)C)C(C)C.CC[O:32]CC>>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH:18]=[O:32])[CH:15]3[CH2:16][CH:11]4[CH2:12][CH:13]([CH2:17][CH:9]2[CH2:10]4)[CH2:14]3)=[CH:4][CH:3]=1

Participants

Reactant 3

HCID 3283Diethyl Ether

HCID 21225700Diisobutylaluminumhydride

HCID 22609685HCID 22609685, compound

Product 1

HCID 22609695HCID 22609695, compoundYield 86%

Conditions

Temperature: 0 °C

Procedure

A flame dried flask under argon was charged with 2-(4-methylphenyl)adamantane-2-carbonitrile (5.90 g, 23.5 mmol) and anhydrous ether (120 mL) and the solution was cooled to 0° C. Diisobutylaluminium hydride (47 mL, 46.9 mmol, 1-M in heptane) was added dropwise and the reaction left to warm to room temperature. After stirring for 1 h the reaction mixture was quenched with dilute HCl (20 mL) and then filtered through celite. The filtrate was partitioned between EtOAc (100 mL) and water (100 mL), separated, dried (MgSO4) and concentrated in vacuo to afford the title compound (5.11 g, 86%) as a white solid: mp 93-97° C.: NMR δH(400 MHz, CDCl3) 1.61-1.64 (2H, d, J 12.8 Hz), 1.71 (2H, br s), 1.78-1.97 (8H, m), 2.33 (3H, s), 2.86 (2H, br s), 7.18-7.20 (2H, d, J 8.4 Hz), 7.25-7.27 (2H, dd, J 2, 8.4 Hz) and 9.27 (1H, s); Retention time 7.99 min (λ=220 nm).

Workup

customA flame dried flask under argon
waitthe reaction left
temperatureto warm to room temperature
customwas quenched with dilute HCl (20 mL)
filtrationfiltered through celite
customThe filtrate was partitioned between EtOAc (100 mL) and water (100 mL)
customseparated
dry with materialdried (MgSO4)
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-e54a3ad5a08e4e0880208558daaa8006
Source dataset: uspto-grants-2004_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06828318B2

Reaction notes

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