Methyl Salicylate → 2-(2-{3-[(E)-2-(7-Chloro-quinolin-2-yl)-vinyl]-phenyl}-2-cyclopropyl-methoxy-ethoxy)-benzoic acid methyl ester

HRID 512923Notes

Reaction equation

HRID 512923 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8](/[CH:12]=[CH:13]/[C:14]3[CH:15]=[C:16]([CH:20]([CH:25]4[CH2:27][CH2:26]4)[CH:21](OC)[OH:22])[CH:17]=[CH:18][CH:19]=3)=[N:9]2)=[CH:4][CH:3]=1.[C:28]([O:37][CH3:38])(=[O:36])[C:29]1[C:30](=[CH:32][CH:33]=[CH:34][CH:35]=1)O.N(C(OC(C)C)=O)=N[C:41](OC(C)C)=[O:42].ClCCl>C1COCC1>[CH3:38][O:37][C:28](=[O:36])[C:29]1[CH:30]=[CH:32][CH:33]=[CH:34][C:35]=1[O:22][CH2:21][C:20]([O:42][CH3:41])([C:16]1[CH:17]=[CH:18][CH:19]=[C:14](/[CH:13]=[CH:12]/[C:8]2[CH:7]=[CH:6][C:5]3[C:4](=[CH:3][C:2]([Cl:1])=[CH:11][CH:10]=3)[N:9]=2)[CH:15]=1)[CH:25]1[CH2:26][CH2:27]1

Participants

6

Reactant 4

HCID 4133Methyl SalicylateHCID 6344DichloromethaneHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 867207352-{3-[(E)-2-(7-chloro-quinolin-2-yl)-vinyl]-phenyl}-2-cyclopropyl methoxy-ethanol

Product 1

HCID 1317332782-(2-{3-[(E)-2-(7-Chloro-quinolin-2-yl)-vinyl]-phenyl}-2-cyclopropyl-methoxy-ethoxy)-benzoic acid methyl esterYield 9.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of ether-alcohol 44 (0.9 g, 0.0024 mol) in THF (5 ml) was added triphenyl phosphene (0.93 g, 0.0035 mol) and methyl salicylate (0.54 ml, 0.0036 mol). The resulting mixture was stirred at ambient temperature for 5 minutes and diisopropyl azodicarboxilate (0.71 g, 0.0035 mol) was added drop wise to the mixture. The reaction mixture was stirred at the same temperature for seven days. Dichloromethane (30 ml) was added to the mixture followed by drying of the resulted solution over sodium sulfate, evaporation of the solvents and FC to give ester 45 (0.12 g, 9.62%).

Workup

  1. stirringThe reaction mixture was stirred at the same temperature for seven days
  2. dry with materialby drying of the resulted solution over sodium sulfate, evaporation of the solvents and FC

Sources & evidence

ORD record
ord-b7039e9b02744d678f858c9add7671f1
Source dataset
uspto-grants-2015_08
Patent number
US09102665B2

Reaction notes

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