Triphenylphosphine → 4-(3-Cyclopentyloxy-4-methoxyphenyl)-4-(2-[4-(2-hydroxyethan-1-oxy)phenyl]ethynyl)-1,1-(ethylenedioxy)cyclohexane

HRID 343566

Reaction equation

HRID 343566 reaction equation
[OH:1][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8](I)=[CH:7][CH:6]=1.[CH:12]1([O:17][C:18]2[CH:19]=[C:20]([C:26]3([C:36]#[CH:37])[CH2:31][CH2:30][C:29]4([O:35][CH2:34][CH2:33][O:32]4)[CH2:28][CH2:27]3)[CH:21]=[CH:22][C:23]=2[O:24][CH3:25])[CH2:16][CH2:15][CH2:14][CH2:13]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>N1CCCCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:12]1([O:17][C:18]2[CH:19]=[C:20]([C:26]3([C:36]#[C:37][C:8]4[CH:9]=[CH:10][C:5]([O:4][CH2:3][CH2:2][OH:1])=[CH:6][CH:7]=4)[CH2:31][CH2:30][C:29]4([O:32][CH2:33][CH2:34][O:35]4)[CH2:28][CH2:27]3)[CH:21]=[CH:22][C:23]=2[O:24][CH3:25])[CH2:13][CH2:14][CH2:15][CH2:16]1

Participants

6

Reactant 3

HCID 11776TriphenylphosphineHCID 35132082-(4-Iodophenoxy)ethanolHCID 110895964-(3-Cyclopentyloxy-4-methoxyphenyl)-1,1-(ethylenedioxy)-4-ethynylcyclohexane

Product 1

HCID 541798624-(3-Cyclopentyloxy-4-methoxyphenyl)-4-(2-[4-(2-hydroxyethan-1-oxy)phenyl]ethynyl)-1,1-(ethylenedioxy)cyclohexane

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8082PiperidineSolvent

Procedure

A solution of 4-(2-hydroxyethoxy)phenyl iodide (0.059 g, 0.22 mmol), and 4-(3-cyclopentyloxy-4-methoxyphenyl)-1,1-(ethylenedioxy)-4-ethynylcyclohexane (0.080 g, 0.22 nmol) in dry piperidine (1 mL) was treated with a mixture of tetrakis(triphenylphosphine)palladium (0.013 g, 0.011 mmol), cuprous iodide (0.0025 g, 0.013 mmol), and triphenylphosphine (crystal), as described above in Example 11. Purification of the crude product by chromatography (silica gel, 1 to 2% methanol in methylene chloride) followed by pumping in vacuo afforded the titled intermediate as a viscous oil. 1H-NMR (400 MHz, CDCl3) δ 7.39 (d, J=9.0 Hz, 2H), 7.24 (d, J=2.1 Hz, 1H), 7.13 (d-d, J=8.3 Hz, J=2.1 Hz, 1H), 6.85 (d, J=8.7, 2H), 6.84 (d, J=8.3 Hz, 1H), 4.81 (p, J=2.0 Hz, 1H), 4.09 (t, J=4.4 Hz, 2H), 4.00 (s, 4H), 3.97 (t, J=4.4 Hz, 2H), 3.84 (s, 3H), 2.3 to 1.5 (m, 21H with H2O).

Workup

  1. customPurification of the crude product by chromatography (silica gel, 1 to 2% methanol in methylene chloride)

Sources & evidence

ORD record
ord-4b56e8e3b034477b8d9b5cb306c0e014
Source dataset
uspto-grants-1999_01
Patent number
US05861421

Linked notes

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