Triphenylphosphine → 2-[(5-Hexynyl)oxy]benzenepropanoic acid methyl ester

HRID 327987

반응식

HRID 327987 반응식
[CH2:1](O)[CH2:2][CH2:3][CH2:4][C:5]#[CH:6].[CH3:8][O:9][C:10](=[O:20])[CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[OH:19].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[CH3:8][O:9][C:10](=[O:20])[CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[O:19][CH2:6][CH2:5][CH2:4][CH2:3][C:2]#[CH:1]

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 702345-Hexyn-1-olHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 2794569Methyl 3-(2-hydroxyphenyl)propionate

생성물 1

HCID 537894482-[(5-Hexynyl)oxy]benzenepropanoic acid methyl ester수율 77%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A mixture of 0.98 g (10 mmol) of 5-hexyn-1-ol, 1.98 g (11 mmol) of 2-hydroxybenzenepropanoic acid methyl ester, 2.88 g (11 mmol) of triphenylphosphine, 1.91 g (11 mmol) of diethyl azodicarboxylate, and 220 mL of dry tetrahydrofuran was stirred at room temperature for 100 hr and then concentrated under reduced pressure. The residue was triturated with 9:1 hexane-ether. The solid was filtered with suction and washed with the same solvent mixture. The filtrate and washes were combined and concentrated in vacuo. Flash chromatography of the residue on silica gel, eluting with 9:1 hexane-ether gave 2 g (77%) of 2[(5-hexynyl)oxy]benzenepropanoic acid methyl ester as a colorless oil.

후처리

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was triturated with 9:1 hexane-ether
  3. filtrationThe solid was filtered with suction
  4. washwashed with the same solvent mixture
  5. concentrationconcentrated in vacuo
  6. washFlash chromatography of the residue on silica gel, eluting with 9:1 hexane-ether

출처 및 근거

ORD 기록
ord-c4f18eed0fca40d3832b567c6507aed1
출처 데이터셋
uspto-grants-1993_12
특허 번호
US05273999

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