Water → 7-Cyano-1,2,3,4-tetrahydro-naphthalen-1-ol

HRID 2089472Notes

Reaction equation

Br[C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH2:8][CH:9]2[OH:12])=[CH:4][CH:3]=1.O.C(OCC)C.[CH3:19][N:20](C=O)C>[C-]#N.[Zn+2].[C-]#N.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:19]([C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH2:8][CH:9]2[OH:12])=[CH:4][CH:3]=1)#[N:20]

Participants

Conditions

Temperature: 95 °C

Procedure

To a solution of 7-bromo-1,2,3,4-tetrahydro-naphthalen-1-ol (0.708 g, 3.11 mmol), which can be prepared as described in Example 5, in DMF (6.5 mL) is added zinc cyanide (0.274 g, 2.33 mmol). Four evacuation-nitrogen fill cycles are performed and tetrakis(triphenylphosphine) palladium (0.072 g, 0.062 mmol) is added. The mixture is heated to 95° C. until the reaction is complete, whereupon water and diethyl ether are added. The mixture is filtered through Celite® and the organic phase is washed with water, dried with MgSO4, filtered and concentrated to give 7-cyano-1,2,3,4-tetrahydro-naphthalen-1-ol; 1H NMR (400 MHz, CDCl3) δ ppm 1.76-1.92 (m, 2 H), 1.95-2.13 (m, 2 H), 2.73-2.94 (m, 2 H), 4.77-4.80 (m, 1 H), 7.20 (d, J=8.0 Hz, 1 H), 7.46 (dd, J=8.0, 1.6 Hz, 1 H), 7.79 (br. s, 1 H).

Workup

additionare added
filtrationThe mixture is filtered through Celite®
washthe organic phase is washed with water
dry with materialdried with MgSO4
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-4cf5a92626824bb48a354dfda6cb2de8
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08436035B2

Reaction notes

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