Triethylamine → HCID 19386519, compound

HRID 2399212Notes

Reaction equation

HRID 2399212 reaction equation
[C:1]([CH:3]1[CH2:12][CH2:11][C:6]2([O:10][CH2:9][CH2:8][O:7]2)[CH2:5][CH2:4]1)#[CH:2].Br[C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)=[CH:16][CH:15]=1.C(N(CC)CC)C>C(OCC)C.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.[Cu]Br>[F:26][C:23]1[CH:22]=[CH:21][C:20]([C:17]2[CH:18]=[CH:19][C:14]([C:2]#[C:1][CH:3]3[CH2:12][CH2:11][C:6]4([O:7][CH2:8][CH2:9][O:10]4)[CH2:5][CH2:4]3)=[CH:15][CH:16]=2)=[CH:25][CH:24]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 968824-Bromo-4'-fluoro-1,1'-biphenylHCID 197052738-Ethynyl-1,4-dioxaspiro[4.5]decane

Product 1

HCID 19386519HCID 19386519, compound

Reagents, catalysts & solvents 3

HCID 24593copper(I) bromideCatalystHCID 178418397HCID 178418397, compoundCatalystHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 1.03 g of 8-ethynyl-1,4-dioxaspiro[4.5]decane, 1.197 g 4-bromo-4'-fluorobiphenyl, 0.11 g of tetrakis(triphenylphosphine)palladium, 0.041 g of copper(I) bromide and 45 ml of triethylamine was heated to boiling for 4.5 hours. After cooling the mixture was diluted with diethyl ether, washed twice with water, dried over sodium sulphate, filtered and concentrated. The crude 8-[(4'-fluoro-4-biphenylyl)ethynyl]-1,4-dioxaspiro[4.5]decane (1.82. g) obtained was purified by chromatography on 35 g of silica gel with hexane/ethyl acetate (vol. 9:1). Yield 1.30 g.

Workup

  1. temperaturewas heated
  2. temperatureAfter cooling the mixture
  3. washwashed twice with water
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-2c260b19e850493e959d0e7065878baa
Source dataset
uspto-grants-1995_09
Patent number
US05447657

Reaction notes

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