Triphenylphosphine → HCID 54023069, compound

HRID 361302Notes

Reaction equation

[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[C:7]([O:11][CH3:12])[CH:6]=[CH:5][C:4]=1[C@@H:13]1[CH2:18][CH2:17][CH2:16][CH2:15][C@H:14]1[C:19]([NH2:21])=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1.C(Cl)(Cl)(Cl)Cl.C(OCC)(=O)C>[C:19]([C@@H:14]1[CH2:15][CH2:16][CH2:17][CH2:18][C@H:13]1[C:4]1[CH:5]=[CH:6][C:7]([O:11][CH3:12])=[C:8]([O:9][CH3:10])[C:3]=1[O:2][CH3:1])#[N:21]

Participants

Conditions

Temperature: 50 °C

Procedure

To a stirred solution of 1.05 g (3.58 mmol) of trans-2-(2,3,4-trimethoxyphenyl)-cyclohexane-1-carboxamide in 5 mL of THF and 5 mL of CCl4 was added 1.88 g (7.17 mmol) of triphenylphosphine. The mixture was stirred at 50° C. for 2 h. The mixture was diluted with 70 mL of ethyl acetate, washed with 50 mL of 5% aqueous HCl and 50 mL of saturated aqueous NaHCO3, and dried over MgSO4. Removal of the solvent left 2.38 g of a tan solid which was purified by flash chromatography on a column of 30 g of silica gel eluted successively with 100 mL portions of 0, 10, 20, 30, 40, 50 and 60% ether in hexanes to afford 0.77 g of trans-1-cyano-2-(2,3,4-trimethoxyphenyl)cyclohexane (Example 42) as a white solid, mp 69°-72° C.

Workup

washwashed with 50 mL of 5% aqueous HCl and 50 mL of saturated aqueous NaHCO3
dry with materialdried over MgSO4
customRemoval of the solvent
waitleft 2.38 g of a tan solid which
customwas purified by flash chromatography on a column of 30 g of silica gel
washeluted successively with 100 mL portions of 0, 10, 20, 30, 40, 50 and 60% ether in hexanes

Sources & evidence

ORD record: ord-3c6c0024d9bb4f05a192849dcb1ff3de
Source dataset: uspto-grants-1999_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05866513

Reaction notes

Loading…