HCID 22709072, compound → HCID 22709073, compound

HRID 352267Notes

Reaction equation

HRID 352267 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][OH:19])[CH:6]=[CH:5]2.[O:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH:21]1[O:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][O:33][C:34]1[CH:39]=[CH:38][C:37]([C:40]#[CH:41])=[CH:36][CH:35]=1>C(N(CC)CC)C.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[O:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH:21]1[O:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][O:33][C:34]1[CH:35]=[CH:36][C:37]([C:40]#[C:41][C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[CH:8]=[C:7]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][OH:19])[CH:6]=[CH:5]3)=[CH:38][CH:39]=1

Participants

7

Reactant 2

HCID 22709072HCID 22709072, compoundHCID 22709077HCID 22709077, compound

Product 1

HCID 22709073HCID 22709073, compoundYield 51.5%

Reagents, catalysts & solvents 4

HCID 11776TriphenylphosphineCatalystHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8471TriethylamineSolvent

Procedure

A degassed mixture of pure 6-(6-bromonaphthalen-2-yloxy)hexan-1-ol (5.88 g), 4-[6-(tetrahydropyran-2-yloxy)hexyloxy]phenyl acetylene (6.05 g), triphenylphosphine (0.21 g), copper(I) iodide (0.04 g) and bis(triphenylphosphine)palladium dichloride (0.14 g) in 60 ml of triethylamine was refluxed for 2 hours under an atmosphere of argon. The reaction mixture was cooled and filtered though celite to give a yellowish solution which was then evaporated to dryness to give a yellow residue, which was purified by chromatography using a silica gel column and cyclohexane/ethyl acetate (2:1, 1:1) as eluent, followed by recrystallisation of the resulting solid from cyclohexane/ethyl acetate (100 ml/3 ml) to give 5.10 g of 6-[6-[4-[6-(tetra-hydropyran-2-yloxy)hexyloxy]phenylethyny]naphthalen-2-yloxy]hexan-1-ol as a white powder.

Workup

  1. temperaturewas refluxed for 2 hours under an atmosphere of argon
  2. temperatureThe reaction mixture was cooled
  3. filtrationfiltered though celite
  4. customto give a yellowish solution which
  5. customwas then evaporated to dryness
  6. customto give a yellow residue, which
  7. customwas purified by chromatography
  8. customfollowed by recrystallisation of the resulting solid from cyclohexane/ethyl acetate (100 ml/3 ml)

Sources & evidence

ORD record
ord-6e0ea0e753474b19b6fccdddbae10c07
Source dataset
uspto-grants-2004_06
Patent number
US06746729B1

Reaction notes

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