Triphenylphosphine → HCID 57007951, compound

HRID 482504Notes

Reaction equation

HRID 482504 reaction equation
[C:1]12([C:11]3[CH:12]=[C:13]([C:24]#[CH:25])[CH:14]=[CH:15][C:16]=3[O:17][CH2:18][O:19][CH2:20][CH2:21][O:22][CH3:23])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.Br[C:27]1[CH:34]=[CH:33][C:30]([CH:31]=[O:32])=[CH:29][CH:28]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(N(CC)CC)C>[C:1]12([C:11]3[CH:12]=[C:13]([C:24]#[C:25][C:27]4[CH:34]=[CH:33][C:30]([CH:31]=[O:32])=[CH:29][CH:28]=4)[CH:14]=[CH:15][C:16]=3[O:17][CH2:18][O:19][CH2:20][CH2:21][O:22][CH3:23])[CH2:2][CH:3]3[CH2:9][CH:7]([CH2:6][CH:5]([CH2:4]3)[CH2:10]1)[CH2:8]2

Participants

6

Reactant 3

HCID 11776TriphenylphosphineHCID 707414-BromobenzaldehydeHCID 57056393HCID 57056393, compound

Product 1

HCID 57007951HCID 57007951, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 8471TriethylamineSolvent

Procedure

3 g (8.8 mmol) of 3-(1-adamantyl)-4-methoxyethoxymethoxyphenylacetylene, 1.8 g (9.7 mmol) of 4-bromobenzaldehyde and 50 ml of triethylamine were introduced into a three-necked flask. The reaction mixture was degassed with nitrogen for 15 min, 160 mg (1.7 mmol) of palladium(II) acetate and 350 mg (1.3 mmol) of triphenylphosphine were added and stirring was carried out at room temperature for twelve hours. The reaction mixture was evaporated to dryness, the residue was taken up in water and ethyl ether and the organic phase was separated by settling, dried over magnesium sulfate and evaporated.

Workup

  1. customThe reaction mixture was degassed with nitrogen for 15 min
  2. waitwas carried out at room temperature for twelve hours
  3. customThe reaction mixture was evaporated to dryness
  4. customethyl ether and the organic phase was separated
  5. dry with materialdried over magnesium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-9dfb4348739340e7ac7b4b03a7d756e1
Source dataset
uspto-grants-1998_08
Patent number
US05798354

Reaction notes

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