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1,3-Propanediol → 3-[5-Methyl-3-(2-methyl-5-nitrophenylsulfonyloxy)phenoxy]propanol

HRID 442948
ノート
印刷プレビュー

反応式

HRID 442948 の反応式
[CH3:1][C:2]1[CH:3]=[C:4]([O:9][S:10]([C:13]2[CH:18]=[C:17]([N+:19]([O-:21])=[O:20])[CH:16]=[CH:15][C:14]=2[CH3:22])(=[O:12])=[O:11])[CH:5]=[C:6]([OH:8])[CH:7]=1.C(P(CCCC)CCCC)CCC.[CH2:36](O)[CH2:37][CH2:38][OH:39].N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>O1CCCC1.CCCCCC>[CH3:1][C:2]1[CH:3]=[C:4]([O:9][S:10]([C:13]2[CH:18]=[C:17]([N+:19]([O-:21])=[O:20])[CH:16]=[CH:15][C:14]=2[CH3:22])(=[O:12])=[O:11])[CH:5]=[C:6]([CH:7]=1)[O:8][CH2:36][CH2:37][CH2:38][OH:39]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 104421,3-PropanediolHCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 544160485-Methyl-3-(2-methyl-5-nitrophenylsulfonyloxy)phenol

生成物 1

HCID 537902373-[5-Methyl-3-(2-methyl-5-nitrophenylsulfonyloxy)phenoxy]propanol収率 48.2%

試薬・触媒・溶媒 2

HCID 8028
Tetrahydrofuran
溶媒
HCID 8058Hexane溶媒

実験手順

To a solution of 5-methyl-3-(2-methyl-5-nitrophenylsulfonyloxy)phenol (1.46 g, 5.0 mmol), as prepared in the preceding step, tri-n-butylphosphine (1.6 g, 8.0 mmol) and 1,3-propanediol (2.3 g, 30 mmol) in anhydrous tetrahydrofuran (50 mL) was added 1,1'-(azodicarbonyl)dipiperidine (2.0 g, 8.0 mmol). The mixture was stirred at ambient temperature overnight. Hexane (80 mL) was added to the mixture, and the precipitates were removed by filtration. The filtrate was evaporated in vacuo, and the residue was purified by flash column chromatography (1:1 hexane/ethyl acetate) to give the title compound as a yellow oil (920 mg, 48%). 1H-NMR (300 MHz, CDCl3) δ 8.72 (s, 1H), 8.37 (d, J=8.3 Hz, 1H), 7.62 (d, J=8.4 Hz, 1H), 6.63 (s, 1H), 6.43 (s, 1H), 6.40 (s, 1H), 4.02 (t, J=6.0 Hz, 2H), 3.81 (t, J=6.0 Hz, 2H), 2.89 (s, 3H), 2.25 (s, 3H), 1.99 (m, 2H), 1.58 (s, 1H).

後処理

  1. customthe precipitates were removed by filtration
  2. customThe filtrate was evaporated in vacuo
  3. customthe residue was purified by flash column chromatography (1:1 hexane/ethyl acetate)

出典と根拠

ORDレコード
ord-c2dcf1e1073745dc8134804d0d77cc1a
出典データセット
uspto-grants-1999_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05891909

反応ノート

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