Triphenylphosphine → HCID 20745894、化合物

HRID 2308122ノート

反応式

HRID 2308122 の反応式
[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][OH:8].[CH3:9][O:10][C:11](=[O:23])[C:12]1[CH:21]=[C:20](O)[CH:19]=[C:14]([C:15]([O:17][CH3:18])=[O:16])[CH:13]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(OC(N=NC(OCC)=O)=O)C>O1CCCC1.C1(C)C=CC=CC=1>[CH3:18][O:17][C:15](=[O:16])[C:14]1[CH:19]=[C:20]([O:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][Cl:1])[CH:21]=[C:12]([C:11]([O:10][CH3:9])=[O:23])[CH:13]=1

参加物

7

反応物 4

HCID 11776TriphenylphosphineHCID 748286-Chloro-1-hexanolHCID 830651,3-Benzenedicarboxylic acid, 5-hydroxy-, 1,3-dimethyl esterHCID 220568ethyl N-ethoxycarbonyliminocarbamate

生成物 1

HCID 20745894HCID 20745894、化合物収率 55%

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

13.02 g (95.3 mmol) of 6-chlorohexanol were added to a solution of 20.04 g (95.3 mmol) of 5-hydroxyisophthalic acid dimethyl ester and 47.4 g (180.5 mmol) of triphenylphosphine in 300 ml of tetrahydrofuran. The colourless solution was cooled to 0° C. and then 79 ml (180.5 mmol) of a 40% solution of azodicarboxylic acid diethyl ester in toluene were added dropwise over a period of 2 hours and 45 minutes. The mixture was allowed to react for another 30 minutes at 0° C. and then for 22 hours at room temperature. The reaction mixture was concentrated by evaporation under vacuum. The residue was filtered through silica gel using dichloromethane:diethylether (85:15) as eluent. The filtrate was concentrated in vacuum and further purified by column chromatography on silica gel with hexane:ethyl acetate (9:1) to give 17.12 g (55%) of 5-[(6-chlorohexyl)oxy]isophthalic acid dimethyl ester as a white solid.

後処理

  1. customto react for another 30 minutes at 0° C.
  2. concentrationThe reaction mixture was concentrated by evaporation under vacuum
  3. filtrationThe residue was filtered through silica gel
  4. concentrationThe filtrate was concentrated in vacuum
  5. customfurther purified by column chromatography on silica gel with hexane:ethyl acetate (9:1)

出典と根拠

ORDレコード
ord-42cb82dd8dac4a64ad9fb6c5795cefef
出典データセット
uspto-grants-2004_12
特許番号
US06833421B1

反応ノート

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