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

HRID 974281노트

반응식

HRID 974281 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

HCID 5280541(E)-Hexadec-2-enal수율 75%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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+).

후처리

  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)

출처 및 근거

ORD 기록
ord-ed4a570280814ac7b04ba84b901a04fe
출처 데이터셋
uspto-grants-1991_11
특허 번호
US05068345

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