3-Thiophenecarboxaldehyde → (E)-4-(3-thienyl)-3-buten-1-ol

HRID 1464750노트

반응식

HRID 1464750 반응식
[Br-].[OH:2][CH2:3][CH2:4][CH2:5][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CCCCCC.C([Li])CCC.[S:36]1[CH:40]=[CH:39][C:38]([CH:41]=O)=[CH:37]1>O1CCCC1>[S:36]1[CH:40]=[CH:39][C:38](/[CH:41]=[CH:5]/[CH2:4][CH2:3][OH:2])=[CH:37]1

참가 물질

5

반응물 3

HCID 681353-ThiophenecarboxaldehydeHCID 11025793Phosphonium, (3-hydroxypropyl)triphenyl-, bromideHCID 178418244HCID 178418244, 화합물

생성물 1

HCID 19916993(E)-4-(3-thienyl)-3-buten-1-ol수율 7.5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

1.0 g of (3-hydroxypropyl)triphenylphosphonium bromide was dissolved in 20 ml of tetrahydrofuran, and under ice cooling, 3.4 ml of a 15% n-butyllithiumhexane solution was added. After the mixture was stirred for 30 minutes, 270 mg of 3-thiophenecarboxaldhyde was added. The mixture was stirred for 30 minutes, and then the solvent was evaporated. The residue was worked up in a customary manner, and purified by silica gel column chromatography [benzene/ethyl acetate=6/1] to give 28 mg (yield 7%) of the captioned compound as a colorless oil.

후처리

  1. stirringThe mixture was stirred for 30 minutes
  2. customthe solvent was evaporated
  3. custompurified by silica gel column chromatography [benzene/ethyl acetate=6/1]

출처 및 근거

ORD 기록
ord-29de806acdf2497bb9b2ed46e09f67b1
출처 데이터셋
uspto-grants-1994_04
특허 번호
US05306728

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