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

HRID 442985

Reaction equation

HRID 442985 reaction equation
[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]

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-6edec1c327304fdaac86baa095a07d6a
Source dataset
uspto-grants-1999_04
Patent number
US05891909

Linked notes

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