(E)-3-[Ethoxy(4-phenylbutyl)phosphinyl]-2-propenoic acid, methyl ester → trans-6-[Ethoxy(4-phenylbutyl)phosphinyl]-3-cyclohexene-1-carboxylic acid, methyl ester

HRID 231885ノート

反応式

HRID 231885 の反応式
[CH2:1]([O:3][P:4]([CH2:12][CH2:13][CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)(/[CH:6]=[CH:7]/[C:8]([O:10][CH3:11])=[O:9])=[O:5])[CH3:2]>C1(C)C=CC=CC=1>[CH2:1]([O:3][P:4]([CH2:12][CH2:13][CH2:14][CH2:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)([C@H:6]1[C@H:7]([C:8]([O:10][CH3:11])=[O:9])[CH2:15][CH:14]=[CH:13][CH2:12]1)=[O:5])[CH3:2]

参加物

3

反応物 1

HCID 14518130(E)-3-[Ethoxy(4-phenylbutyl)phosphinyl]-2-propenoic acid, methyl ester

生成物 1

HCID 86743237trans-6-[Ethoxy(4-phenylbutyl)phosphinyl]-3-cyclohexene-1-carboxylic acid, methyl ester収率 118.9%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
-78 °C

実験手順

A solution of the title compound from Example 1A (3.72 g, 12.0 mmols) in a minimum amount of toluene (ca 5 ml) was transferred to a 25×150 mm glass tube which served as a liner of a stainless steel Parr pressure bomb. The bomb and its contained tube were cooled to -78° C. and a stream of butadiene was bubbled through the mixture until the glass tube was nearly full. The pressure bomb was then quickly sealed and allowed to warm to room temperature. The bomb and its contents were then heated to 100° C. and maintained at that temperature for 24 hours, after which they were cooled to room temperature. The pressure was released from the bomb and methanol was added to the contents, resulting in a gelatinous precipitate. The precipitate was removed by filtration and the filtrate was concentrated to a clear oil (3.52 g) The oil was chromatographed on LPS-1 silica gel, eluting with ethyl acetate, to give the title compound (2.6 g, 59%, Rf 0.2).

後処理

  1. customa stream of butadiene was bubbled through the mixture until the glass tube
  2. customThe pressure bomb was then quickly sealed
  3. temperatureto warm to room temperature
  4. temperatureThe bomb and its contents were then heated to 100° C.
  5. temperaturemaintained at that temperature for 24 hours
  6. temperatureafter which they were cooled to room temperature
  7. additionwas added to the contents
  8. customresulting in a gelatinous precipitate
  9. customThe precipitate was removed by filtration
  10. concentrationthe filtrate was concentrated to a clear oil (3.52 g) The oil
  11. customwas chromatographed on LPS-1 silica gel
  12. washeluting with ethyl acetate

出典と根拠

ORDレコード
ord-214a46a8b316488fb1721414d5ea208a
出典データセット
uspto-grants-1989_07
特許番号
US04849525

反応ノート

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