Water → 2-[(Hexadecyloxy)methyl]-4-penten-1-ol

HRID 248158ノート

反応式

HRID 248158 の反応式
[H-].[Na+].[CH2:3]([OH:8])CCC=C.[CH2:9]([O:25][C:26]1[CH:35]=[C:34](C)[CH:33]=[CH:32]C=1S([O-])(=O)=O)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24].O>CN(C)C=O.O1CCCC1>[CH2:9]([O:25][CH2:26][CH:35]([CH2:34][CH:33]=[CH2:32])[CH2:3][OH:8])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]

参加物

7

反応物 4

HCID 962WaterHCID 131814-Penten-1-OLHCID 24758Sodium hydrideHCID 19764414HCID 19764414、化合物

生成物 1

HCID 147858282-[(Hexadecyloxy)methyl]-4-penten-1-ol収率 10.9%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
80 °C

実験手順

To a suspension of 19.1 g of 50% sodium hydride under argon in 300 ml of N,N-dimethylformamide is added dropwise over a period of 1 hour, with stirring a solution of 37 g of 4-penten-1-ol, 2-methanol (prepared as described by B. K. Wasson, et. al., J. Chem. Soc., 39, 923 (1961)) in 200 ml of tetrahydrofuran. After stirring another 30 minutes, 126.34 g of hexadecyloxytosylate is added followed by 500 ml of tetrahydrofuran. This mixture is stirred for 2.5 hours, then heated to 80° C. for 20 minutes and then at room temperature overnight. Water is added and the mixture extracted with ether. The ether extract is dried and then evaporated. The residue is distilled using a Kugelrohr. The fraction distilling at 200°-210° C. 1 mm is collected, purified by chromatography and then redistilled, to give 11.35 g of the desired compound.

後処理

  1. additionis added dropwise over a period of 1 hour
  2. stirringThis mixture is stirred for 2.5 hours
  3. customat room temperature
  4. customovernight
  5. extractionthe mixture extracted with ether
  6. extractionThe ether extract
  7. customis dried
  8. customevaporated
  9. distillationThe residue is distilled
  10. distillationThe fraction distilling at 200°-210° C
  11. custom1 mm is collected
  12. custompurified by chromatography
  13. distillationredistilled

出典と根拠

ORDレコード
ord-3402bc0cebab48a88639ec72101a89f7
出典データセット
uspto-grants-1993_05
特許番号
US05208223

反応ノート

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