Triphenylphosphine → 4-(6-Hydroxyhexyloxy)-3-methoxycinnamic acid methyl ester

HRID 1250800

反応式

HRID 1250800 の反応式
C([O:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]O)=C.[CH3:11][O:12][C:13](=[O:25])/[CH:14]=[CH:15]/[C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[C:18]([O:23][CH3:24])[CH:17]=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.S(=O)(=O)(O)O.CO>[CH3:11][O:12][C:13](=[O:25])[CH:14]=[CH:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][OH:3])=[C:18]([O:23][CH3:24])[CH:17]=1

参加物

9

反応物 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 5357283Methyl FerulateHCID 220261996-(Ethenyloxy)-1-hexanol

生成物 1

HCID 541470624-(6-Hydroxyhexyloxy)-3-methoxycinnamic acid methyl ester収率 82.8%

試薬・触媒・溶媒 4

HCID 1118Sulfuric Acid触媒HCID 887Methanol溶媒HCID 1140Toluene溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

3.92 ml (25.2 mmol) of 1,6-hexanediol vinyl ether were added to a solution of 5.0 g (24.0 mmol) of (E)-4-hydroxy-3-methoxycinnamic acid methyl ester and 6.61 g (25.2 mmol) of triphenylphosphine in 150 ml of tetrahydrofuran. The colourless solution was subsequently cooled to 0° C. and then 11.5 ml (25.3 mmol) of a 40% solution of azodicarboxylic acid diethyl ester in toluene were added dropwise thereto in the course of 30 minutes. The mixture was subsequently allowed to react first for 30 minutes at 0° C. and then for 22.5 hours at room temperature. 150 ml of methanol and 10 drops of concentrated sulphuric acid were then added to the reaction solution and the mixture was stirred for 1.5 hours. The reaction mixture was then partitioned between ethyl acetate and water; the organic phase was washed with a saturated sodium bicarbonate solution and repeatedly with saturated sodium chloride solution, dried over magnesium sulphate, filtered and concentrated by evaporation. Chromatography of the residue on 470 g of silica gel using toluene/ethyl acetate 1:1 and subsequent crystallisation from ethyl acetate/hexane 3:5 yielded 6.13 g of 4-(6-hydroxyhexyloxy)-3-methoxycinnamic acid methyl ester.

後処理

  1. customin the course of 30 minutes
  2. customto react first for 30 minutes at 0° C.
  3. customThe reaction mixture was then partitioned between ethyl acetate and water
  4. washthe organic phase was washed with a saturated sodium bicarbonate solution and repeatedly with saturated sodium chloride solution
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated by evaporation
  8. customtoluene/ethyl acetate 1:1 and subsequent crystallisation from ethyl acetate/hexane 3:5

出典と根拠

ORDレコード
ord-fdfd1fd62e9d40e9aaec8bbe69797535
出典データセット
uspto-grants-2002_01
特許番号
US06340506B1

関連ノート

読み込み中…