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

HRID 491604

反応式

HRID 491604 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-28a019f4643e4d9d9af8d63730c19b3c
出典データセット
uspto-grants-2009_05
特許番号
US07531553B2

関連ノート

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