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

HRID 1648035

反応式

HRID 1648035 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-ca4921c997bc4acaa14a72107dae2424
出典データセット
uspto-grants-1995_07
特許番号
US05434186

関連ノート

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