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

HRID 2106865노트

반응식

HRID 2106865 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 8021Diethylamine용매

실험 절차

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) (Feuerstein and Heimann, Ber., 34, 1468 (1901)) in anhydrous diethylamine (250 ml). 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 magnesium 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.

후처리

  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 magnesium sulphate
  6. customRemoval of solvents

출처 및 근거

ORD 기록
ord-f6f7c2401f334854a5847823a69938c6
출처 데이터셋
uspto-grants-1990_06
특허 번호
US04931469

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