Cornforth reagent → (E)-Hexadec-2-enal

HRID 974281ノート

反応式

HRID 974281 の反応式
[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[CH2:22]([OH:38])/[CH:23]=[CH:24]/[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37]>ClCCl>[CH:22](=[O:38])/[CH:23]=[CH:24]/[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37]

参加物

4

反応物 2

HCID 2724130Cornforth reagentHCID 5362706(E)-Hexadec-2-en-1-ol

生成物 1

HCID 5280541(E)-Hexadec-2-enal収率 75%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a stirred suspension of 60.6 g (0.161 mol) pyridinium dichromate in 100 mL of dichloromethane was added 25.7 g (0.107 mol) of trans-2-hexadecenol. After 4 h at 25° C., the mixture was filtered (through Celite diatomaceous earth) and the resulting brown solution refiltered through Florisil, an activated magnesium silicate in the form of hard, porous, stable, white granules that are free from dusting sold by Floridin Co. The colorless solution obtained was concentrated in vacuo to 21.8 g (86%) of a white solid. Distillation (90°-100° C./0.40-0.45 torr) provided 19.1 g (75%) of pure trans-2-hexadecenal as a white waxy solid. IR (thin film as melt) 2920, 2850, 1695, 1465, 975 cm-1 ; 1H NMR (CDCl3, 300 MHz) δ9.53 (d, 1, J=6.7 Hz, CHO), 6.88 (overlapping dt, 1, J=15.7, 6.7 Hz, OHCCH=), 1.53 (m, 2, CH 2 CH3), 1.1-1.2 (m, 20, CH2CH2CH2), 0.90 (t, 3, J=7 Hz, CH2CH3). Rf (15% ethyl acetate:hexanes):trans-2-hexadecenol, 0.19 trans-2-hexadecenal, 0.44. MS(FD) m/e 238 (M+).

後処理

  1. filtrationthe mixture was filtered (through Celite diatomaceous earth)
  2. customThe colorless solution obtained
  3. concentrationwas concentrated in vacuo to 21.8 g (86%) of a white solid
  4. distillationDistillation (90°-100° C./0.40-0.45 torr)

出典と根拠

ORDレコード
ord-ed4a570280814ac7b04ba84b901a04fe
出典データセット
uspto-grants-1991_11
特許番号
US05068345

反応ノート

読み込み中…