Hydrochloric Acid → 1-(Hexadecyloxy)but-3-EN-2-OL

HRID 255963

反応式

HRID 255963 の反応式
[Mg].[CH:2](Br)=[CH2:3].[CH2:5]([O:21][CH2:22][CH:23]=[O:24])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].Cl>O1CCCC1.BrC(Br)C.CCOCC>[CH2:5]([O:21][CH2:22][CH:23]([OH:24])[CH:2]=[CH2:3])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 11641BromoetheneHCID 5462224Magnesium2 回HCID 14785848(Hexadecyloxy) acetaldehyde

生成物 1

HCID 139590711-(Hexadecyloxy)but-3-EN-2-OL収率 41.5%

試薬・触媒・溶媒 3

HCID 112011,1-Dibromoethane触媒HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒3 回

反応条件

温度
0 °C

実験手順

To a stirring mixture of 5.67 g of magnesium in 25 ml of tetrahydrofuran was added 10 drops of dibromoethane as an initiator. After the reaction began another 100 ml of tetrahydrofuran was added followed by the dropwise addition of a solution of 49.85 g of vinyl bromide in 250 ml of tetrahydrofuran at a rate to maintain reflux. After all of the magnesium had reacted, the solution was cooled to 0° C. and a solution of 44.2 g of (hexadecyloxy) acetaldehyde, prepared by the procedure of Example 3, in 175 ml of ether was added dropwise over 1/2 hour. After 1 hour at room temperature dilute hydrochloric acid was added. The tetrahydrofuran was removed and the residue was extracted with ether. The ether layer was washed with brine, dried and the solvent removed. The residue was purified by HPLC [hexane: ether (9:1), two columns, two passes] giving an oil which was distilled via a Kugelrohr apparatus (185°-190° C., 0.2 mm) giving a colorles oil which solidified on standing to give 20.17 g of the desired compound.

後処理

  1. additionwas added
  2. temperatureto maintain
  3. temperaturereflux
  4. additionwas added dropwise over 1/2 hour
  5. customThe tetrahydrofuran was removed
  6. extractionthe residue was extracted with ether
  7. washThe ether layer was washed with brine
  8. customdried
  9. customthe solvent removed
  10. customThe residue was purified by HPLC [hexane: ether (9:1), two columns, two passes]
  11. customgiving an oil which
  12. distillationwas distilled via a Kugelrohr apparatus (185°-190° C., 0.2 mm)
  13. customgiving a colorles oil which

出典と根拠

ORDレコード
ord-41414b2cf6584599ac72779c5a79dd96
出典データセット
uspto-grants-1987_10
特許番号
US04699990

関連ノート

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