Acetyl chloride → 4-Acetoxy-2-(3-cyclopentyloxy-4-methoxybenzyl)-benzoxazole

HRID 1377549Notes

Reaction equation

HRID 1377549 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:21]=[CH:22][C:23]=2[O:24][CH3:25])[CH2:10][C:11]2[O:12][C:13]3[CH:19]=[CH:18][CH:17]=[C:16]([OH:20])[C:14]=3[N:15]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:26](Cl)(=[O:28])[CH3:27]>N1C=CC=CC=1.CO>[C:26]([O:20][C:16]1[C:14]2[N:15]=[C:11]([CH2:10][C:9]3[CH:21]=[CH:22][C:23]([O:24][CH3:25])=[C:7]([O:6][CH:1]4[CH2:5][CH2:4][CH2:3][CH2:2]4)[CH:8]=3)[O:12][C:13]=2[CH:19]=[CH:18][CH:17]=1)(=[O:28])[CH3:27]

Participants

5

Reactant 2

HCID 6367Acetyl chlorideHCID 99677292-(3-Cyclopentyloxy-4-methoxybenzyl)-4-hydroxybenzoxazole

Product 1

HCID 101344364-Acetoxy-2-(3-cyclopentyloxy-4-methoxybenzyl)-benzoxazoleYield 53%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1049PyridineSolvent

Procedure

A solution of 2-(3-cyclopentyloxy-4-methoxybenzyl)-4-hydroxybenzoxazole (200 mg) and acetyl chloride (84 μl) in pyridine (6 ml) was stirred at room temperature, under nitrogen, for 3 hours. The reaction mixture was diluted with methanol (20 ml) and evaporated in-vacuo to yield a yellow solid. The solid was purified by flash chromatography (SiO2 ; dichloromethane; methanol (50:1)) and crystallized from ether/petroleum ether to yield the title compound (119 mg, 53%) as a white crystalline solid (mp 65-°67° C.). δH (250MHZ;d6DMSO) 1.45-1.92 (8H,m,4×CH2), 2.35 (3H,s,MeC(O)), 3.70 (3H,s,OMe), 4.24 (2H,s,CH2), 4.73 (1H,m,CH), 6.82 (1H,dd,ArH), 6.89 (1H,d,ArH), 6.95 (1H,d,ArH), 7.12 (1H,dd,ArH), 7.36 (1H,t,ArH), 7.58 (1H,dd,ArH).

Workup

  1. customevaporated in-vacuo
  2. customto yield a yellow solid
  3. customThe solid was purified by flash chromatography (SiO2 ; dichloromethane; methanol (50:1))
  4. customcrystallized from ether/petroleum ether

Sources & evidence

ORD record
ord-3b1eab153d04492996270ca72678ef9e
Source dataset
uspto-grants-1997_09
Patent number
US05665737

Reaction notes

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