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

HRID 1722227ノート

反応式

HRID 1722227 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8021Diethylamine溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-dbc8bf3db7934775b6edefad0366b4bf
出典データセット
uspto-grants-1989_08
特許番号
US04855086

反応ノート

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