Tetrahydrofurfuryl alcohol → 2-(2-Chloro-5-nitro-phenoxymethyl)-tetrahydrofuran

HRID 491604

반응식

HRID 491604 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[OH:11].[CH2:12](O)[CH:13]1[O:17][CH2:16][CH2:15][CH2:14]1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[O:11][CH2:12][CH:13]1[CH2:14][CH2:15][CH2:16][O:17]1

참가 물질

6

반응물 4

HCID 7360Tetrahydrofurfuryl alcoholHCID 11776TriphenylphosphineHCID 692642-Chloro-5-nitrophenolHCID 5363146Diisopropyl azodicarboxylate

생성물 1

HCID 690160502-(2-Chloro-5-nitro-phenoxymethyl)-tetrahydrofuran

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 2-chloro-5-nitrophenol (3.39 g, 19.52 mmol), tetrahydrofurfuryl alcohol (1.99 g, 19.52 mmol), and Ph3P (5.12 g, 19.52 mmol) in 34 ml THF, cooled to −15° C., was added dropwise, over 90 min, a solution of DIAD (4.15 g, 20.5 mmol). The reaction was warmed to RT and stirred for 18 h. The reaction was concentrated to dryness. The crude residue was treated with a small mix of Et2O and hexanes and sonicated so as to triturate out bulk of impurities, which were filtered off. The filtrate was concentrated to dryness. The resulting residue was purified by silica gel column chromatography using EtOAc in hexanes to elute the title compound.

후처리

  1. additionwas added dropwise, over 90 min
  2. concentrationThe reaction was concentrated to dryness
  3. additionThe crude residue was treated with
  4. additiona small mix of Et2O and hexanes
  5. customsonicated so as
  6. customto triturate out bulk of impurities, which
  7. filtrationwere filtered off
  8. concentrationThe filtrate was concentrated to dryness
  9. customThe resulting residue was purified by silica gel column chromatography
  10. washto elute the title compound

출처 및 근거

ORD 기록
ord-28a019f4643e4d9d9af8d63730c19b3c
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07531553B2

연결된 노트

불러오는 중…