Tributylphosphine → [1-[3-(2-Cyanophenylsulfonyloxy)-5-methylphenoxy]methyl]-cyclopropylmethanol

HRID 442985

反応式

HRID 442985 の反応式
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9]([O:12][C:13]1[CH:14]=[C:15]([OH:20])[CH:16]=[C:17]([CH3:19])[CH:18]=1)(=[O:11])=[O:10])#[N:2].[CH2:21](P(CCCC)CCCC)CCC.[OH:34][CH2:35][C:36]1(CO)[CH2:38][CH2:37]1.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>O1CCCC1.CCCCCC>[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9]([O:12][C:13]1[CH:14]=[C:15]([CH:16]=[C:17]([CH3:19])[CH:18]=1)[O:20][CH2:21][CH:35]([CH:36]1[CH2:38][CH2:37]1)[OH:34])(=[O:11])=[O:10])#[N:2]

参加物

7

反応物 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 41014371,1-Bis(hydroxymethyl)cyclopropaneHCID 227226433-(2-Cyanophenylsulfonyloxy)-5-methylphenol

生成物 1

HCID 53878000[1-[3-(2-Cyanophenylsulfonyloxy)-5-methylphenoxy]methyl]-cyclopropylmethanol収率 62%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8058Hexane溶媒

実験手順

To a solution of 3-(2-cyanophenylsulfonyloxy)-5-methylphenol (1.45 g, 5.0 mmol), as prepared in the step a of example 13), tri-n-butylphosphine (1.62 g, 8.0 mmol) and 1,1-dihydroxymethylcyclopropane (1.52 g, 15 mmol), as prepared in U.S. Pat. No. 5,472,964, in anhydrous tetrahydrofuran (50 mL) was added 1,1'-(azodicarbonyl)dipiperidine (2.02, 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 (10% ethyl acetate in dichloromethane) to give the title compound as a white solid (1.15, 62%). 1H-NMR (300 MHz, CDCl3) δ 8.09 (m, 1H), 7.93 (m, 1H), 7.80 (m, 2H), 6.66 (s, 1H), 6.60 (s, 1H), 6.56 (s, 1H), 3.86 (s, 2H), 3.60 (s, 2H), 2.26 (s, 3H), 1.85 (br s, 1H), 0.62 (s, 4H).

後処理

  1. customas prepared in U.S
  2. customthe precipitates were removed by filtration
  3. customThe filtrate was evaporated in vacuo
  4. customthe residue was purified by flash column chromatography (10% ethyl acetate in dichloromethane)

出典と根拠

ORDレコード
ord-6edec1c327304fdaac86baa095a07d6a
出典データセット
uspto-grants-1999_04
特許番号
US05891909

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