4-Pentyn-1-ol → 7-phenyl-hept-4-yn-6E-en-1-ol

HRID 1722227Notes

Reaction equation

HRID 1722227 reaction equation
[CH2:1]([OH:6])[CH2:2][CH2:3][C:4]#[CH:5].[CH:7](/Br)=[CH:8]\[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C(NCC)C>[C:9]1(/[CH:8]=[CH:7]/[C:5]#[C:4][CH2:3][CH2:2][CH2:1][OH:6])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 793464-Pentyn-1-olHCID 5314126trans-beta-Bromostyrene

Product 1

HCID 117887007-phenyl-hept-4-yn-6E-en-1-olYield 87.1%

Reagents, catalysts & solvents 1

HCID 8021DiethylamineSolvent

Procedure

Cuprous iodide (0.4 g, 2.1 mmol) and bis-triphenylphosphine palladium (II) chloride (0.8 g, 1.14 mmol) were added to a solution of pent-4-yn-1-ol (16 g, 193 mmol) (Jones, Eglinton, and Whiting, Org. Syn. Coll., 4, 755, (1963)) and E-styryl bromide (34.34 g, 188 mmol) (Feurerstein and Heimann, Ber., 34, 1468 (1901)) in anhydrous diethylamine (250 m). The whole was stirred under an atmosphere of dry nitrogen with the exclusion of moisture and light for 16 hours. The diethylamine was removed at reduced pressure and the residue diluted with water (500 ml). The aqueous mixture was extracted with ether. The ethereal extracts were passed down a column composed of silica (100 g), Celite (trade name, from Koch-light Ltd) (100 g) and activated charcoal (20 g) at 3 psi (21 KPa) pressure. The column was washed with ether (200 ml) and the combined organic extracts dried over anhydrous magensium sulphate. Removal of solvents gave 30.5 g of 7-phenyl-hept-4-yn-6E-en-1-ol as a pale brown oil. The material was not purified further.

Workup

  1. customThe diethylamine was removed at reduced pressure
  2. additionthe residue diluted with water (500 ml)
  3. extractionThe aqueous mixture was extracted with ether
  4. washThe column was washed with ether (200 ml)
  5. dry with materialthe combined organic extracts dried over anhydrous magensium sulphate
  6. customRemoval of solvents

Sources & evidence

ORD record
ord-dbc8bf3db7934775b6edefad0366b4bf
Source dataset
uspto-grants-1989_08
Patent number
US04855086

Reaction notes

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