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

HRID 442985

반응식

HRID 442985 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8058Hexane용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-6edec1c327304fdaac86baa095a07d6a
출처 데이터셋
uspto-grants-1999_04
특허 번호
US05891909

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